Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds

Natural products are a main source of new chemical entities for use in drug and pesticide discovery. In order to discover lead compounds with high herbicidal activity, a series of new pyrido[2,3-<i<d</i<] pyrimidine derivatives were designed and synthesized using 2-chloronicotinic acid a...
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Autor*in:	Lijing Min [verfasserIn] Wei Liang [verfasserIn] Joanna Bajsa-Hirschel [verfasserIn] Peng Ye [verfasserIn] Qiao Wang [verfasserIn] Xinpeng Sun [verfasserIn] Charles L. Cantrell [verfasserIn] Liang Han [verfasserIn] Nabo Sun [verfasserIn] Stephen O. Duke [verfasserIn] Xinghai Liu [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2023

Schlagwörter:	natural product uracil pyrido[2,3- one-pot synthesis herbicidal activity protoporphyrinogen oxidase

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 28(2023), 21, p 7363
Übergeordnetes Werk:	volume:28 ; year:2023 ; number:21, p 7363

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules28217363

Katalog-ID:	DOAJ095449817

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allfields	10.3390/molecules28217363 doi (DE-627)DOAJ095449817 (DE-599)DOAJ1536895760e54fe2bfc8d1268ae93b7c DE-627 ger DE-627 rakwb eng QD241-441 Lijing Min verfasserin aut Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Natural products are a main source of new chemical entities for use in drug and pesticide discovery. In order to discover lead compounds with high herbicidal activity, a series of new pyrido[2,3-<i<d</i<] pyrimidine derivatives were designed and synthesized using 2-chloronicotinic acid as the starting material. Their structures were characterized with <sup<1</sup<H NMR, <sup<13</sup<C NMR and HRMS, and the herbicidal activities against dicotyledonous lettuce (<i<Lactuca sativa</i<), field mustard (<i<Brassica campestris</i<), monocotyledonous bentgrass (<i<Agrostis stolonifera</i<) and wheat (<i<Triticum aestivum</i<) were determined. The results indicated that most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives had no marked inhibitory effect on lettuce at 1 mM. However, most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives possessed good activity against bentgrass at 1 mM. Among them, the most active compound, 3-methyl-1-(2,3,4-trifluorophenyl)pyrido[2,3-<i<d</i<]pyrimidine-2,4(1<i<H</i<,3<i<H</i<)-dione (<b<2o</b<), was as active as the positive controls, the commercial herbicides clomazone and flumioxazin. Molecular simulation was performed with molecular docking and DFT calculations. The docking studies provided strong evidence that <b<2o</b< acts as an herbicide by inhibition of protoporphyrinogen oxidase. However, the physiological results indicate that it does not act on this target in vivo, implying that it could be metabolically converted to a compound with a different molecular target. natural product uracil pyrido[2,3-<i<d</i<] pyrimidine derivatives one-pot synthesis herbicidal activity protoporphyrinogen oxidase Organic chemistry Wei Liang verfasserin aut Joanna Bajsa-Hirschel verfasserin aut Peng Ye verfasserin aut Qiao Wang verfasserin aut Xinpeng Sun verfasserin aut Charles L. Cantrell verfasserin aut Liang Han verfasserin aut Nabo Sun verfasserin aut Stephen O. Duke verfasserin aut Xinghai Liu verfasserin aut In Molecules MDPI AG, 2003 28(2023), 21, p 7363 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:21, p 7363 https://doi.org/10.3390/molecules28217363 kostenfrei https://doaj.org/article/1536895760e54fe2bfc8d1268ae93b7c kostenfrei https://www.mdpi.com/1420-3049/28/21/7363 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 21, p 7363
spelling	10.3390/molecules28217363 doi (DE-627)DOAJ095449817 (DE-599)DOAJ1536895760e54fe2bfc8d1268ae93b7c DE-627 ger DE-627 rakwb eng QD241-441 Lijing Min verfasserin aut Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Natural products are a main source of new chemical entities for use in drug and pesticide discovery. In order to discover lead compounds with high herbicidal activity, a series of new pyrido[2,3-<i<d</i<] pyrimidine derivatives were designed and synthesized using 2-chloronicotinic acid as the starting material. Their structures were characterized with <sup<1</sup<H NMR, <sup<13</sup<C NMR and HRMS, and the herbicidal activities against dicotyledonous lettuce (<i<Lactuca sativa</i<), field mustard (<i<Brassica campestris</i<), monocotyledonous bentgrass (<i<Agrostis stolonifera</i<) and wheat (<i<Triticum aestivum</i<) were determined. The results indicated that most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives had no marked inhibitory effect on lettuce at 1 mM. However, most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives possessed good activity against bentgrass at 1 mM. Among them, the most active compound, 3-methyl-1-(2,3,4-trifluorophenyl)pyrido[2,3-<i<d</i<]pyrimidine-2,4(1<i<H</i<,3<i<H</i<)-dione (<b<2o</b<), was as active as the positive controls, the commercial herbicides clomazone and flumioxazin. Molecular simulation was performed with molecular docking and DFT calculations. The docking studies provided strong evidence that <b<2o</b< acts as an herbicide by inhibition of protoporphyrinogen oxidase. However, the physiological results indicate that it does not act on this target in vivo, implying that it could be metabolically converted to a compound with a different molecular target. natural product uracil pyrido[2,3-<i<d</i<] pyrimidine derivatives one-pot synthesis herbicidal activity protoporphyrinogen oxidase Organic chemistry Wei Liang verfasserin aut Joanna Bajsa-Hirschel verfasserin aut Peng Ye verfasserin aut Qiao Wang verfasserin aut Xinpeng Sun verfasserin aut Charles L. Cantrell verfasserin aut Liang Han verfasserin aut Nabo Sun verfasserin aut Stephen O. Duke verfasserin aut Xinghai Liu verfasserin aut In Molecules MDPI AG, 2003 28(2023), 21, p 7363 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:21, p 7363 https://doi.org/10.3390/molecules28217363 kostenfrei https://doaj.org/article/1536895760e54fe2bfc8d1268ae93b7c kostenfrei https://www.mdpi.com/1420-3049/28/21/7363 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 21, p 7363
allfields_unstemmed	10.3390/molecules28217363 doi (DE-627)DOAJ095449817 (DE-599)DOAJ1536895760e54fe2bfc8d1268ae93b7c DE-627 ger DE-627 rakwb eng QD241-441 Lijing Min verfasserin aut Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Natural products are a main source of new chemical entities for use in drug and pesticide discovery. In order to discover lead compounds with high herbicidal activity, a series of new pyrido[2,3-<i<d</i<] pyrimidine derivatives were designed and synthesized using 2-chloronicotinic acid as the starting material. Their structures were characterized with <sup<1</sup<H NMR, <sup<13</sup<C NMR and HRMS, and the herbicidal activities against dicotyledonous lettuce (<i<Lactuca sativa</i<), field mustard (<i<Brassica campestris</i<), monocotyledonous bentgrass (<i<Agrostis stolonifera</i<) and wheat (<i<Triticum aestivum</i<) were determined. The results indicated that most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives had no marked inhibitory effect on lettuce at 1 mM. However, most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives possessed good activity against bentgrass at 1 mM. Among them, the most active compound, 3-methyl-1-(2,3,4-trifluorophenyl)pyrido[2,3-<i<d</i<]pyrimidine-2,4(1<i<H</i<,3<i<H</i<)-dione (<b<2o</b<), was as active as the positive controls, the commercial herbicides clomazone and flumioxazin. Molecular simulation was performed with molecular docking and DFT calculations. The docking studies provided strong evidence that <b<2o</b< acts as an herbicide by inhibition of protoporphyrinogen oxidase. However, the physiological results indicate that it does not act on this target in vivo, implying that it could be metabolically converted to a compound with a different molecular target. natural product uracil pyrido[2,3-<i<d</i<] pyrimidine derivatives one-pot synthesis herbicidal activity protoporphyrinogen oxidase Organic chemistry Wei Liang verfasserin aut Joanna Bajsa-Hirschel verfasserin aut Peng Ye verfasserin aut Qiao Wang verfasserin aut Xinpeng Sun verfasserin aut Charles L. Cantrell verfasserin aut Liang Han verfasserin aut Nabo Sun verfasserin aut Stephen O. Duke verfasserin aut Xinghai Liu verfasserin aut In Molecules MDPI AG, 2003 28(2023), 21, p 7363 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:21, p 7363 https://doi.org/10.3390/molecules28217363 kostenfrei https://doaj.org/article/1536895760e54fe2bfc8d1268ae93b7c kostenfrei https://www.mdpi.com/1420-3049/28/21/7363 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 21, p 7363
allfieldsGer	10.3390/molecules28217363 doi (DE-627)DOAJ095449817 (DE-599)DOAJ1536895760e54fe2bfc8d1268ae93b7c DE-627 ger DE-627 rakwb eng QD241-441 Lijing Min verfasserin aut Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Natural products are a main source of new chemical entities for use in drug and pesticide discovery. In order to discover lead compounds with high herbicidal activity, a series of new pyrido[2,3-<i<d</i<] pyrimidine derivatives were designed and synthesized using 2-chloronicotinic acid as the starting material. Their structures were characterized with <sup<1</sup<H NMR, <sup<13</sup<C NMR and HRMS, and the herbicidal activities against dicotyledonous lettuce (<i<Lactuca sativa</i<), field mustard (<i<Brassica campestris</i<), monocotyledonous bentgrass (<i<Agrostis stolonifera</i<) and wheat (<i<Triticum aestivum</i<) were determined. The results indicated that most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives had no marked inhibitory effect on lettuce at 1 mM. However, most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives possessed good activity against bentgrass at 1 mM. Among them, the most active compound, 3-methyl-1-(2,3,4-trifluorophenyl)pyrido[2,3-<i<d</i<]pyrimidine-2,4(1<i<H</i<,3<i<H</i<)-dione (<b<2o</b<), was as active as the positive controls, the commercial herbicides clomazone and flumioxazin. Molecular simulation was performed with molecular docking and DFT calculations. The docking studies provided strong evidence that <b<2o</b< acts as an herbicide by inhibition of protoporphyrinogen oxidase. However, the physiological results indicate that it does not act on this target in vivo, implying that it could be metabolically converted to a compound with a different molecular target. natural product uracil pyrido[2,3-<i<d</i<] pyrimidine derivatives one-pot synthesis herbicidal activity protoporphyrinogen oxidase Organic chemistry Wei Liang verfasserin aut Joanna Bajsa-Hirschel verfasserin aut Peng Ye verfasserin aut Qiao Wang verfasserin aut Xinpeng Sun verfasserin aut Charles L. Cantrell verfasserin aut Liang Han verfasserin aut Nabo Sun verfasserin aut Stephen O. Duke verfasserin aut Xinghai Liu verfasserin aut In Molecules MDPI AG, 2003 28(2023), 21, p 7363 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:21, p 7363 https://doi.org/10.3390/molecules28217363 kostenfrei https://doaj.org/article/1536895760e54fe2bfc8d1268ae93b7c kostenfrei https://www.mdpi.com/1420-3049/28/21/7363 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 21, p 7363
allfieldsSound	10.3390/molecules28217363 doi (DE-627)DOAJ095449817 (DE-599)DOAJ1536895760e54fe2bfc8d1268ae93b7c DE-627 ger DE-627 rakwb eng QD241-441 Lijing Min verfasserin aut Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Natural products are a main source of new chemical entities for use in drug and pesticide discovery. In order to discover lead compounds with high herbicidal activity, a series of new pyrido[2,3-<i<d</i<] pyrimidine derivatives were designed and synthesized using 2-chloronicotinic acid as the starting material. Their structures were characterized with <sup<1</sup<H NMR, <sup<13</sup<C NMR and HRMS, and the herbicidal activities against dicotyledonous lettuce (<i<Lactuca sativa</i<), field mustard (<i<Brassica campestris</i<), monocotyledonous bentgrass (<i<Agrostis stolonifera</i<) and wheat (<i<Triticum aestivum</i<) were determined. The results indicated that most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives had no marked inhibitory effect on lettuce at 1 mM. However, most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives possessed good activity against bentgrass at 1 mM. Among them, the most active compound, 3-methyl-1-(2,3,4-trifluorophenyl)pyrido[2,3-<i<d</i<]pyrimidine-2,4(1<i<H</i<,3<i<H</i<)-dione (<b<2o</b<), was as active as the positive controls, the commercial herbicides clomazone and flumioxazin. Molecular simulation was performed with molecular docking and DFT calculations. The docking studies provided strong evidence that <b<2o</b< acts as an herbicide by inhibition of protoporphyrinogen oxidase. However, the physiological results indicate that it does not act on this target in vivo, implying that it could be metabolically converted to a compound with a different molecular target. natural product uracil pyrido[2,3-<i<d</i<] pyrimidine derivatives one-pot synthesis herbicidal activity protoporphyrinogen oxidase Organic chemistry Wei Liang verfasserin aut Joanna Bajsa-Hirschel verfasserin aut Peng Ye verfasserin aut Qiao Wang verfasserin aut Xinpeng Sun verfasserin aut Charles L. Cantrell verfasserin aut Liang Han verfasserin aut Nabo Sun verfasserin aut Stephen O. Duke verfasserin aut Xinghai Liu verfasserin aut In Molecules MDPI AG, 2003 28(2023), 21, p 7363 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:21, p 7363 https://doi.org/10.3390/molecules28217363 kostenfrei https://doaj.org/article/1536895760e54fe2bfc8d1268ae93b7c kostenfrei https://www.mdpi.com/1420-3049/28/21/7363 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 21, p 7363
language	English
source	In Molecules 28(2023), 21, p 7363 volume:28 year:2023 number:21, p 7363
sourceStr	In Molecules 28(2023), 21, p 7363 volume:28 year:2023 number:21, p 7363
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	natural product uracil pyrido[2,3-<i<d</i<] pyrimidine derivatives one-pot synthesis herbicidal activity protoporphyrinogen oxidase Organic chemistry
isfreeaccess_bool	true
container_title	Molecules
authorswithroles_txt_mv	Lijing Min @@aut@@ Wei Liang @@aut@@ Joanna Bajsa-Hirschel @@aut@@ Peng Ye @@aut@@ Qiao Wang @@aut@@ Xinpeng Sun @@aut@@ Charles L. Cantrell @@aut@@ Liang Han @@aut@@ Nabo Sun @@aut@@ Stephen O. Duke @@aut@@ Xinghai Liu @@aut@@
publishDateDaySort_date	2023-01-01T00:00:00Z
hierarchy_top_id	311313132
id	DOAJ095449817
language_de	englisch
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In order to discover lead compounds with high herbicidal activity, a series of new pyrido[2,3-<i<d</i<] pyrimidine derivatives were designed and synthesized using 2-chloronicotinic acid as the starting material. Their structures were characterized with <sup<1</sup<H NMR, <sup<13</sup<C NMR and HRMS, and the herbicidal activities against dicotyledonous lettuce (<i<Lactuca sativa</i<), field mustard (<i<Brassica campestris</i<), monocotyledonous bentgrass (<i<Agrostis stolonifera</i<) and wheat (<i<Triticum aestivum</i<) were determined. The results indicated that most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives had no marked inhibitory effect on lettuce at 1 mM. However, most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives possessed good activity against bentgrass at 1 mM. 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callnumber-first	Q - Science
author	Lijing Min
spellingShingle	Lijing Min misc QD241-441 misc natural product misc uracil misc pyrido[2,3-<i<d</i<] pyrimidine derivatives misc one-pot synthesis misc herbicidal activity misc protoporphyrinogen oxidase misc Organic chemistry Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds
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topic_title	QD241-441 Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds natural product uracil pyrido[2,3-<i<d</i<] pyrimidine derivatives one-pot synthesis herbicidal activity protoporphyrinogen oxidase
topic	misc QD241-441 misc natural product misc uracil misc pyrido[2,3-<i<d</i<] pyrimidine derivatives misc one-pot synthesis misc herbicidal activity misc protoporphyrinogen oxidase misc Organic chemistry
topic_unstemmed	misc QD241-441 misc natural product misc uracil misc pyrido[2,3-<i<d</i<] pyrimidine derivatives misc one-pot synthesis misc herbicidal activity misc protoporphyrinogen oxidase misc Organic chemistry
topic_browse	misc QD241-441 misc natural product misc uracil misc pyrido[2,3-<i<d</i<] pyrimidine derivatives misc one-pot synthesis misc herbicidal activity misc protoporphyrinogen oxidase misc Organic chemistry
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title	Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds
ctrlnum	(DE-627)DOAJ095449817 (DE-599)DOAJ1536895760e54fe2bfc8d1268ae93b7c
title_full	Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds
author_sort	Lijing Min
journal	Molecules
journalStr	Molecules
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author_browse	Lijing Min Wei Liang Joanna Bajsa-Hirschel Peng Ye Qiao Wang Xinpeng Sun Charles L. Cantrell Liang Han Nabo Sun Stephen O. Duke Xinghai Liu
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class	QD241-441
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author-letter	Lijing Min
doi_str_mv	10.3390/molecules28217363
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title_sort	synthesis, herbicidal activity, mode of action, and in silico analysis of novel pyrido[2,3-<i<d</i<]pyrimidine compounds
callnumber	QD241-441
title_auth	Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds
abstract	Natural products are a main source of new chemical entities for use in drug and pesticide discovery. In order to discover lead compounds with high herbicidal activity, a series of new pyrido[2,3-<i<d</i<] pyrimidine derivatives were designed and synthesized using 2-chloronicotinic acid as the starting material. Their structures were characterized with <sup<1</sup<H NMR, <sup<13</sup<C NMR and HRMS, and the herbicidal activities against dicotyledonous lettuce (<i<Lactuca sativa</i<), field mustard (<i<Brassica campestris</i<), monocotyledonous bentgrass (<i<Agrostis stolonifera</i<) and wheat (<i<Triticum aestivum</i<) were determined. The results indicated that most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives had no marked inhibitory effect on lettuce at 1 mM. However, most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives possessed good activity against bentgrass at 1 mM. Among them, the most active compound, 3-methyl-1-(2,3,4-trifluorophenyl)pyrido[2,3-<i<d</i<]pyrimidine-2,4(1<i<H</i<,3<i<H</i<)-dione (<b<2o</b<), was as active as the positive controls, the commercial herbicides clomazone and flumioxazin. Molecular simulation was performed with molecular docking and DFT calculations. The docking studies provided strong evidence that <b<2o</b< acts as an herbicide by inhibition of protoporphyrinogen oxidase. However, the physiological results indicate that it does not act on this target in vivo, implying that it could be metabolically converted to a compound with a different molecular target.
abstractGer	Natural products are a main source of new chemical entities for use in drug and pesticide discovery. In order to discover lead compounds with high herbicidal activity, a series of new pyrido[2,3-<i<d</i<] pyrimidine derivatives were designed and synthesized using 2-chloronicotinic acid as the starting material. Their structures were characterized with <sup<1</sup<H NMR, <sup<13</sup<C NMR and HRMS, and the herbicidal activities against dicotyledonous lettuce (<i<Lactuca sativa</i<), field mustard (<i<Brassica campestris</i<), monocotyledonous bentgrass (<i<Agrostis stolonifera</i<) and wheat (<i<Triticum aestivum</i<) were determined. The results indicated that most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives had no marked inhibitory effect on lettuce at 1 mM. However, most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives possessed good activity against bentgrass at 1 mM. Among them, the most active compound, 3-methyl-1-(2,3,4-trifluorophenyl)pyrido[2,3-<i<d</i<]pyrimidine-2,4(1<i<H</i<,3<i<H</i<)-dione (<b<2o</b<), was as active as the positive controls, the commercial herbicides clomazone and flumioxazin. Molecular simulation was performed with molecular docking and DFT calculations. The docking studies provided strong evidence that <b<2o</b< acts as an herbicide by inhibition of protoporphyrinogen oxidase. However, the physiological results indicate that it does not act on this target in vivo, implying that it could be metabolically converted to a compound with a different molecular target.
abstract_unstemmed	Natural products are a main source of new chemical entities for use in drug and pesticide discovery. In order to discover lead compounds with high herbicidal activity, a series of new pyrido[2,3-<i<d</i<] pyrimidine derivatives were designed and synthesized using 2-chloronicotinic acid as the starting material. Their structures were characterized with <sup<1</sup<H NMR, <sup<13</sup<C NMR and HRMS, and the herbicidal activities against dicotyledonous lettuce (<i<Lactuca sativa</i<), field mustard (<i<Brassica campestris</i<), monocotyledonous bentgrass (<i<Agrostis stolonifera</i<) and wheat (<i<Triticum aestivum</i<) were determined. The results indicated that most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives had no marked inhibitory effect on lettuce at 1 mM. However, most of the pyrido[2,3-<i<d</i<] pyrimidine derivatives possessed good activity against bentgrass at 1 mM. Among them, the most active compound, 3-methyl-1-(2,3,4-trifluorophenyl)pyrido[2,3-<i<d</i<]pyrimidine-2,4(1<i<H</i<,3<i<H</i<)-dione (<b<2o</b<), was as active as the positive controls, the commercial herbicides clomazone and flumioxazin. Molecular simulation was performed with molecular docking and DFT calculations. The docking studies provided strong evidence that <b<2o</b< acts as an herbicide by inhibition of protoporphyrinogen oxidase. However, the physiological results indicate that it does not act on this target in vivo, implying that it could be metabolically converted to a compound with a different molecular target.
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title_short	Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds
url	https://doi.org/10.3390/molecules28217363 https://doaj.org/article/1536895760e54fe2bfc8d1268ae93b7c https://www.mdpi.com/1420-3049/28/21/7363 https://doaj.org/toc/1420-3049
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Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-<i<d</i<]pyrimidine Compounds

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