Photoredox-based late-stage functionalization in SAR study for

Glucosylceramide synthase (GCS) has drawn much attention as an attractive protein target in the disease pathways of Parkinson’s Disease (PD) and lysosomal storage disorders, such as Gaucher’s Disease (GD). In previous our study, T-036 and its analogue, 2a, were discovered as novel GCS inhibitors. To...
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Gespeichert in:

Autor*in:	Wang, Junsi [verfasserIn] Reynolds, Matthew [verfasserIn] Ibáñez, Ignacio [verfasserIn] Sasaki, Yusuke [verfasserIn] Tanaka, Yuta [verfasserIn] Kikuchi, Fumiaki [verfasserIn] Ohashi, Tomohiro [verfasserIn] Sato, Sho [verfasserIn] Miyabayashi, Mariko [verfasserIn] Fujii, Takahiro [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2022

Schlagwörter:	Photoredox Late-stage functionalization Structure–activity relationship Glucosylceramide synthase

Übergeordnetes Werk:	Enthalten in: Bioorganic & medicinal chemistry letters - Amsterdam [u.a.] : Elsevier Science, 1991, 77
Übergeordnetes Werk:	volume:77

DOI / URN:	10.1016/j.bmcl.2022.129039

Katalog-ID:	ELV008733015

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520			\|a Glucosylceramide synthase (GCS) has drawn much attention as an attractive protein target in the disease pathways of Parkinson’s Disease (PD) and lysosomal storage disorders, such as Gaucher’s Disease (GD). In previous our study, T-036 and its analogue, 2a, were discovered as novel GCS inhibitors. To further improve activity of this chemical series, SAR was investigated on the fused pyridyl ring core of 2a by employing a photoredox reaction that significantly reduced synthetic demand. Herein, we successfully applied the decarboxylation C–H alkylation photoredox reaction to introduce a wide variety of substituents at the 6-position of the fused pyridine core scaffold. This quick SAR acquisition facilitated the swift identification of the potent GCS inhibitors 2b (IC50 = 5.9 nM) and 2g (IC50 = 3.6 nM). Moreover, 2b exhibited superior in vivo potency to that of our previously reported lead compound, T-036.
650		4	\|a Photoredox
650		4	\|a Late-stage functionalization
650		4	\|a Structure–activity relationship
650		4	\|a Glucosylceramide synthase
700	1		\|a Reynolds, Matthew \|e verfasserin \|4 aut
700	1		\|a Ibáñez, Ignacio \|e verfasserin \|4 aut
700	1		\|a Sasaki, Yusuke \|e verfasserin \|4 aut
700	1		\|a Tanaka, Yuta \|e verfasserin \|4 aut
700	1		\|a Kikuchi, Fumiaki \|e verfasserin \|4 aut
700	1		\|a Ohashi, Tomohiro \|e verfasserin \|4 aut
700	1		\|a Sato, Sho \|e verfasserin \|4 aut
700	1		\|a Miyabayashi, Mariko \|e verfasserin \|4 aut
700	1		\|a Fujii, Takahiro \|e verfasserin \|4 aut
700	1		\|a Tanaka, Yuta \|e verfasserin \|4 aut
773	0	8	\|i Enthalten in \|t Bioorganic & medicinal chemistry letters \|d Amsterdam [u.a.] : Elsevier Science, 1991 \|g 77 \|h Online-Ressource \|w (DE-627)306717522 \|w (DE-600)1501505-1 \|w (DE-576)110916573 \|x 1464-3405 \|7 nnns
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912			\|a GBV_ILN_2034
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936	b	k	\|a 44.42 \|j Pharmazeutische Chemie
951			\|a AR
952			\|d 77

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allfields	10.1016/j.bmcl.2022.129039 doi (DE-627)ELV008733015 (ELSEVIER)S0960-894X(22)00515-7 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Wang, Junsi verfasserin aut Photoredox-based late-stage functionalization in SAR study for 2022 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Glucosylceramide synthase (GCS) has drawn much attention as an attractive protein target in the disease pathways of Parkinson’s Disease (PD) and lysosomal storage disorders, such as Gaucher’s Disease (GD). In previous our study, T-036 and its analogue, 2a, were discovered as novel GCS inhibitors. To further improve activity of this chemical series, SAR was investigated on the fused pyridyl ring core of 2a by employing a photoredox reaction that significantly reduced synthetic demand. Herein, we successfully applied the decarboxylation C–H alkylation photoredox reaction to introduce a wide variety of substituents at the 6-position of the fused pyridine core scaffold. This quick SAR acquisition facilitated the swift identification of the potent GCS inhibitors 2b (IC50 = 5.9 nM) and 2g (IC50 = 3.6 nM). Moreover, 2b exhibited superior in vivo potency to that of our previously reported lead compound, T-036. Photoredox Late-stage functionalization Structure–activity relationship Glucosylceramide synthase Reynolds, Matthew verfasserin aut Ibáñez, Ignacio verfasserin aut Sasaki, Yusuke verfasserin aut Tanaka, Yuta verfasserin aut Kikuchi, Fumiaki verfasserin aut Ohashi, Tomohiro verfasserin aut Sato, Sho verfasserin aut Miyabayashi, Mariko verfasserin aut Fujii, Takahiro verfasserin aut Tanaka, Yuta verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 77 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:77 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 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_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 77
spelling	10.1016/j.bmcl.2022.129039 doi (DE-627)ELV008733015 (ELSEVIER)S0960-894X(22)00515-7 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Wang, Junsi verfasserin aut Photoredox-based late-stage functionalization in SAR study for 2022 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Glucosylceramide synthase (GCS) has drawn much attention as an attractive protein target in the disease pathways of Parkinson’s Disease (PD) and lysosomal storage disorders, such as Gaucher’s Disease (GD). In previous our study, T-036 and its analogue, 2a, were discovered as novel GCS inhibitors. To further improve activity of this chemical series, SAR was investigated on the fused pyridyl ring core of 2a by employing a photoredox reaction that significantly reduced synthetic demand. Herein, we successfully applied the decarboxylation C–H alkylation photoredox reaction to introduce a wide variety of substituents at the 6-position of the fused pyridine core scaffold. This quick SAR acquisition facilitated the swift identification of the potent GCS inhibitors 2b (IC50 = 5.9 nM) and 2g (IC50 = 3.6 nM). Moreover, 2b exhibited superior in vivo potency to that of our previously reported lead compound, T-036. Photoredox Late-stage functionalization Structure–activity relationship Glucosylceramide synthase Reynolds, Matthew verfasserin aut Ibáñez, Ignacio verfasserin aut Sasaki, Yusuke verfasserin aut Tanaka, Yuta verfasserin aut Kikuchi, Fumiaki verfasserin aut Ohashi, Tomohiro verfasserin aut Sato, Sho verfasserin aut Miyabayashi, Mariko verfasserin aut Fujii, Takahiro verfasserin aut Tanaka, Yuta verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 77 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:77 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 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_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 77
allfields_unstemmed	10.1016/j.bmcl.2022.129039 doi (DE-627)ELV008733015 (ELSEVIER)S0960-894X(22)00515-7 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Wang, Junsi verfasserin aut Photoredox-based late-stage functionalization in SAR study for 2022 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Glucosylceramide synthase (GCS) has drawn much attention as an attractive protein target in the disease pathways of Parkinson’s Disease (PD) and lysosomal storage disorders, such as Gaucher’s Disease (GD). In previous our study, T-036 and its analogue, 2a, were discovered as novel GCS inhibitors. To further improve activity of this chemical series, SAR was investigated on the fused pyridyl ring core of 2a by employing a photoredox reaction that significantly reduced synthetic demand. Herein, we successfully applied the decarboxylation C–H alkylation photoredox reaction to introduce a wide variety of substituents at the 6-position of the fused pyridine core scaffold. This quick SAR acquisition facilitated the swift identification of the potent GCS inhibitors 2b (IC50 = 5.9 nM) and 2g (IC50 = 3.6 nM). Moreover, 2b exhibited superior in vivo potency to that of our previously reported lead compound, T-036. Photoredox Late-stage functionalization Structure–activity relationship Glucosylceramide synthase Reynolds, Matthew verfasserin aut Ibáñez, Ignacio verfasserin aut Sasaki, Yusuke verfasserin aut Tanaka, Yuta verfasserin aut Kikuchi, Fumiaki verfasserin aut Ohashi, Tomohiro verfasserin aut Sato, Sho verfasserin aut Miyabayashi, Mariko verfasserin aut Fujii, Takahiro verfasserin aut Tanaka, Yuta verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 77 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:77 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 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_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 77
allfieldsGer	10.1016/j.bmcl.2022.129039 doi (DE-627)ELV008733015 (ELSEVIER)S0960-894X(22)00515-7 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Wang, Junsi verfasserin aut Photoredox-based late-stage functionalization in SAR study for 2022 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Glucosylceramide synthase (GCS) has drawn much attention as an attractive protein target in the disease pathways of Parkinson’s Disease (PD) and lysosomal storage disorders, such as Gaucher’s Disease (GD). In previous our study, T-036 and its analogue, 2a, were discovered as novel GCS inhibitors. To further improve activity of this chemical series, SAR was investigated on the fused pyridyl ring core of 2a by employing a photoredox reaction that significantly reduced synthetic demand. Herein, we successfully applied the decarboxylation C–H alkylation photoredox reaction to introduce a wide variety of substituents at the 6-position of the fused pyridine core scaffold. This quick SAR acquisition facilitated the swift identification of the potent GCS inhibitors 2b (IC50 = 5.9 nM) and 2g (IC50 = 3.6 nM). Moreover, 2b exhibited superior in vivo potency to that of our previously reported lead compound, T-036. Photoredox Late-stage functionalization Structure–activity relationship Glucosylceramide synthase Reynolds, Matthew verfasserin aut Ibáñez, Ignacio verfasserin aut Sasaki, Yusuke verfasserin aut Tanaka, Yuta verfasserin aut Kikuchi, Fumiaki verfasserin aut Ohashi, Tomohiro verfasserin aut Sato, Sho verfasserin aut Miyabayashi, Mariko verfasserin aut Fujii, Takahiro verfasserin aut Tanaka, Yuta verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 77 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:77 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 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_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 77
allfieldsSound	10.1016/j.bmcl.2022.129039 doi (DE-627)ELV008733015 (ELSEVIER)S0960-894X(22)00515-7 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Wang, Junsi verfasserin aut Photoredox-based late-stage functionalization in SAR study for 2022 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Glucosylceramide synthase (GCS) has drawn much attention as an attractive protein target in the disease pathways of Parkinson’s Disease (PD) and lysosomal storage disorders, such as Gaucher’s Disease (GD). In previous our study, T-036 and its analogue, 2a, were discovered as novel GCS inhibitors. To further improve activity of this chemical series, SAR was investigated on the fused pyridyl ring core of 2a by employing a photoredox reaction that significantly reduced synthetic demand. Herein, we successfully applied the decarboxylation C–H alkylation photoredox reaction to introduce a wide variety of substituents at the 6-position of the fused pyridine core scaffold. This quick SAR acquisition facilitated the swift identification of the potent GCS inhibitors 2b (IC50 = 5.9 nM) and 2g (IC50 = 3.6 nM). Moreover, 2b exhibited superior in vivo potency to that of our previously reported lead compound, T-036. Photoredox Late-stage functionalization Structure–activity relationship Glucosylceramide synthase Reynolds, Matthew verfasserin aut Ibáñez, Ignacio verfasserin aut Sasaki, Yusuke verfasserin aut Tanaka, Yuta verfasserin aut Kikuchi, Fumiaki verfasserin aut Ohashi, Tomohiro verfasserin aut Sato, Sho verfasserin aut Miyabayashi, Mariko verfasserin aut Fujii, Takahiro verfasserin aut Tanaka, Yuta verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 77 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:77 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 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_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 77
language	English
source	Enthalten in Bioorganic & medicinal chemistry letters 77 volume:77
sourceStr	Enthalten in Bioorganic & medicinal chemistry letters 77 volume:77
format_phy_str_mv	Article
bklname	Biochemie: Allgemeines Physiologische Chemie Pharmazeutische Chemie
institution	findex.gbv.de
topic_facet	Photoredox Late-stage functionalization Structure–activity relationship Glucosylceramide synthase
dewey-raw	540
isfreeaccess_bool	false
container_title	Bioorganic & medicinal chemistry letters
authorswithroles_txt_mv	Wang, Junsi @@aut@@ Reynolds, Matthew @@aut@@ Ibáñez, Ignacio @@aut@@ Sasaki, Yusuke @@aut@@ Tanaka, Yuta @@aut@@ Kikuchi, Fumiaki @@aut@@ Ohashi, Tomohiro @@aut@@ Sato, Sho @@aut@@ Miyabayashi, Mariko @@aut@@ Fujii, Takahiro @@aut@@
publishDateDaySort_date	2022-01-01T00:00:00Z
hierarchy_top_id	306717522
dewey-sort	3540
id	ELV008733015
language_de	englisch
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author	Wang, Junsi
spellingShingle	Wang, Junsi ddc 540 ssgn 15,3 fid PHARM bkl 35.70 bkl 44.33 bkl 44.42 misc Photoredox misc Late-stage functionalization misc Structure–activity relationship misc Glucosylceramide synthase Photoredox-based late-stage functionalization in SAR study for
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topic_title	540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Photoredox-based late-stage functionalization in SAR study for Photoredox Late-stage functionalization Structure–activity relationship Glucosylceramide synthase
topic	ddc 540 ssgn 15,3 fid PHARM bkl 35.70 bkl 44.33 bkl 44.42 misc Photoredox misc Late-stage functionalization misc Structure–activity relationship misc Glucosylceramide synthase
topic_unstemmed	ddc 540 ssgn 15,3 fid PHARM bkl 35.70 bkl 44.33 bkl 44.42 misc Photoredox misc Late-stage functionalization misc Structure–activity relationship misc Glucosylceramide synthase
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title	Photoredox-based late-stage functionalization in SAR study for
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title_full	Photoredox-based late-stage functionalization in SAR study for
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title_sort	photoredox-based late-stage functionalization in sar study for
title_auth	Photoredox-based late-stage functionalization in SAR study for
abstract	Glucosylceramide synthase (GCS) has drawn much attention as an attractive protein target in the disease pathways of Parkinson’s Disease (PD) and lysosomal storage disorders, such as Gaucher’s Disease (GD). In previous our study, T-036 and its analogue, 2a, were discovered as novel GCS inhibitors. To further improve activity of this chemical series, SAR was investigated on the fused pyridyl ring core of 2a by employing a photoredox reaction that significantly reduced synthetic demand. Herein, we successfully applied the decarboxylation C–H alkylation photoredox reaction to introduce a wide variety of substituents at the 6-position of the fused pyridine core scaffold. This quick SAR acquisition facilitated the swift identification of the potent GCS inhibitors 2b (IC50 = 5.9 nM) and 2g (IC50 = 3.6 nM). Moreover, 2b exhibited superior in vivo potency to that of our previously reported lead compound, T-036.
abstractGer	Glucosylceramide synthase (GCS) has drawn much attention as an attractive protein target in the disease pathways of Parkinson’s Disease (PD) and lysosomal storage disorders, such as Gaucher’s Disease (GD). In previous our study, T-036 and its analogue, 2a, were discovered as novel GCS inhibitors. To further improve activity of this chemical series, SAR was investigated on the fused pyridyl ring core of 2a by employing a photoredox reaction that significantly reduced synthetic demand. Herein, we successfully applied the decarboxylation C–H alkylation photoredox reaction to introduce a wide variety of substituents at the 6-position of the fused pyridine core scaffold. This quick SAR acquisition facilitated the swift identification of the potent GCS inhibitors 2b (IC50 = 5.9 nM) and 2g (IC50 = 3.6 nM). Moreover, 2b exhibited superior in vivo potency to that of our previously reported lead compound, T-036.
abstract_unstemmed	Glucosylceramide synthase (GCS) has drawn much attention as an attractive protein target in the disease pathways of Parkinson’s Disease (PD) and lysosomal storage disorders, such as Gaucher’s Disease (GD). In previous our study, T-036 and its analogue, 2a, were discovered as novel GCS inhibitors. To further improve activity of this chemical series, SAR was investigated on the fused pyridyl ring core of 2a by employing a photoredox reaction that significantly reduced synthetic demand. Herein, we successfully applied the decarboxylation C–H alkylation photoredox reaction to introduce a wide variety of substituents at the 6-position of the fused pyridine core scaffold. This quick SAR acquisition facilitated the swift identification of the potent GCS inhibitors 2b (IC50 = 5.9 nM) and 2g (IC50 = 3.6 nM). Moreover, 2b exhibited superior in vivo potency to that of our previously reported lead compound, T-036.
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title_short	Photoredox-based late-stage functionalization in SAR study for
remote_bool	true
author2	Reynolds, Matthew Ibáñez, Ignacio Sasaki, Yusuke Tanaka, Yuta Kikuchi, Fumiaki Ohashi, Tomohiro Sato, Sho Miyabayashi, Mariko Fujii, Takahiro
author2Str	Reynolds, Matthew Ibáñez, Ignacio Sasaki, Yusuke Tanaka, Yuta Kikuchi, Fumiaki Ohashi, Tomohiro Sato, Sho Miyabayashi, Mariko Fujii, Takahiro
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up_date	2024-07-06T20:43:07.599Z
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