sanglifehrin A | 187148-13-6

分子结构分类

有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物

中文名称

——

中文别名

——

英文名称

sanglifehrin A

英文别名

SfA；(3S,6S,9R,10R,11S,12S,13E,15E,18S,21S)-18-[(2E,4E,8S,9S)-10-[(2S,3R,4S,5S,6R,9S,11S)-9-ethyl-4-hydroxy-3,5,11-trimethyl-8-oxo-1-oxa-7-azaspiro[5.5]undecan-2-yl]-9-hydroxy-8-methyldeca-2,4-dien-2-yl]-10,12-dihydroxy-3-[(3-hydroxyphenyl)methyl]-11-methyl-9-(3-oxobutyl)-6-propan-2-yl-19-oxa-1,4,7,25-tetrazabicyclo[19.3.1]pentacosa-13,15-diene-2,5,8,20-tetrone

CAS

187148-13-6

化学式

C₆₀H₉₁N₅O₁₃

mdl

——

分子量

1090.41

InChiKey

ONJZYZYZIKTIEG-CFBQITSMSA-N

BEILSTEIN

——

EINECS

——

物化性质

密度：

1.23±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

7.3
重原子数：

78
可旋转键数：

15
环数：

5.0
sp3杂化的碳原子比例：

0.67
拓扑面积：

273
氢给体数：

9
氢受体数：

14

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	sanglifehrin A ketal	870465-58-0	C₆₀H₈₉N₅O₁₂	1072.39
——	(4R,7S,10S,16S,19S,21E,23E,25S,26S,27R)-19-[(2E,4E,8S,9S)-10-[(2S,3R,4S,5S,6R,9S,11S)-9-ethyl-4-hydroxy-3,5,11-trimethyl-8-oxo-1-oxa-7-azaspiro[5.5]undecan-2-yl]-9-hydroxy-8-methyldeca-2,4-dien-2-yl]-10-[(3-hydroxyphenyl)methyl]-1,26-dimethyl-7-propan-2-yl-18,28,29-trioxa-6,9,12,30-tetrazatetracyclo[23.3.1.112,16.04,27]triaconta-21,23-diene-5,8,11,17-tetrone	382139-11-9	C₆₀H₈₉N₅O₁₂	1072.39
——	(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-(3-tert-butoxycarbonyloxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester	382139-06-2	C₃₃H₄₄N₄O₉	640.734
——	methyl (3S)-1-[(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-[3-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl]propanoyl]diazinane-3-carboxylate	382138-87-6	C₂₅H₃₈N₄O₇	506.599
——	(2S,3S,4S,5S,6R,9S,11S)-9-ethyl-3,5,11-trimethyl-2-[(2S,3S)-3-methyl-6-(1-phenyltetrazol-5-yl)sulfonyl-2-triethylsilyloxyhexyl]-4-triethylsilyloxy-1-oxa-7-azaspiro[5.5]undecan-8-one	256326-89-3	C₄₀H₇₁N₅O₆SSi₂	806.271
——	(S)-1-[(S)-2-Benzyloxycarbonylamino-3-(3-tert-butoxycarbonyloxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester	382139-05-1	C₂₈H₃₅N₃O₈	541.601
——	(2S,3S,4S,5S,6R,9S,11S)-9-ethyl-3,5,11-trimethyl-2-[(2S,3S)-3-methyl-6-(1-phenyltetrazol-5-yl)sulfanyl-2-triethylsilyloxyhexyl]-4-triethylsilyloxy-1-oxa-7-azaspiro[5.5]undecan-8-one	256326-88-2	C₄₀H₇₁N₅O₄SSi₂	774.272
——	methyl (3S)-1-[(2S)-3-(3-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoyl]diazinane-3-carboxylate	382139-04-0	C₂₃H₂₇N₃O₆	441.484
——	(2S,3R,4S,5S,6R,9S,11S)-9-ethyl-4-hydroxy-2-[(2S,3S)-2-hydroxy-3-methyl-6-(1-phenyltetrazol-5-yl)sulfanylhexyl]-3,5,11-trimethyl-1-oxa-7-azaspiro[5.5]undecan-8-one	256326-87-1	C₂₈H₄₃N₅O₄S	545.747
——	(2S,3S,4S,5S,6R,9S,11S)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(2S,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-methylpent-4-enyl]-9-ethyl-3,5,11-trimethyl-1-oxa-7-azaspiro[5.5]undecan-8-one	247107-76-2	C₃₂H₆₃NO₄Si₂	582.028
——	(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,3S,4S,5S,6R,9S,11S)-4-(tert-butyl-dimethyl-silanyloxy)-9-ethyl-3,5,11-trimethyl-8-oxo-1-oxa-7-aza-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde	275805-45-3	C₃₁H₆₁NO₅Si₂	584.0
——	(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,3S,4S,5S,6R,9S,11S)-4-(tert-butyl-dimethyl-silanyloxy)-9-ethyl-3,5,11-trimethyl-8-oxo-1-oxa-7-aza-spiro[5.5]undec-2-yl]-4-methyl-hexanal	247107-81-9	C₃₃H₆₅NO₅Si₂	612.054
——	(E)-(C4H4NH(CH2CH3)(O)(CH3))C5H4O(CH3)(OH)(CH3)(CH2CH(OH)CH(CH3)CH2CH2CHCHSn(n-butyl)3)	247107-78-4	C₃₄H₆₅NO₄Sn	670.604
——	(2S,3R,4S,5S,6R,9S,11S)-2-((2S,3S)-7-Bromo-2-hydroxy-3-methyl-hept-6-ynyl)-9-ethyl-4-hydroxy-3,5,11-trimethyl-1-oxa-7-aza-spiro[5.5]undecan-8-one	247107-64-8	C₂₂H₃₆BrNO₄	458.436
——	(2S,3R,4S,5S,6R,9S,11S)-9-ethyl-4-hydroxy-2-((2S,3S)-2-hydroxy-3-methylhept-6-yn-1-yl)-3,5,11-trimethyl-1-oxa-7-azaspiro[5.5]undecan-8-one	247107-77-3	C₂₂H₃₇NO₄	379.54
——	2-((2S,3R,4S,5S,6R,9S,11S)-9-ethyl-4-hydroxy-3,5,11-trimethyl-8-oxo-1-oxa-7-azaspiro[5.5]undecan-2-yl)acetaldehyde	247107-56-8	C₁₆H₂₇NO₄	297.395
——	methyl (3S)-1-[(2S)-2-amino-3-[3-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl]propanoyl]diazinane-3-carboxylate	1055029-19-0	C₂₀H₂₉N₃O₆	407.467

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	26(S),27(S)-dihydroxysanglifehrin A	256424-82-5	C₆₀H₉₃N₅O₁₅	1124.42
——	sanglifehrin A ketal	870465-58-0	C₆₀H₈₉N₅O₁₂	1072.39
——	(E)-3-[(3S,6S,9R,10R,11S,12S,13E,15E,18S,21S)-10,12-dihydroxy-3-[(3-hydroxyphenyl)methyl]-11-methyl-2,5,8,20-tetraoxo-9-(3-oxobutyl)-6-propan-2-yl-19-oxa-1,4,7,25-tetrazabicyclo[19.3.1]pentacosa-13,15-dien-18-yl]but-2-enal	256424-81-4	C₃₉H₅₄N₄O₁₀	738.879
——	(2S,3R,4S,5S,6R,9S,11S)-9-ethyl-4-hydroxy-2-[(2S,3S)-2-hydroxy-3-methyl-6-(1-phenyltetrazol-5-yl)sulfanylhexyl]-3,5,11-trimethyl-1-oxa-7-azaspiro[5.5]undecan-8-one	256326-87-1	C₂₈H₄₃N₅O₄S	545.747
——	(2S,3R,4S,5S,6R,9S,11S)-9-ethyl-4-hydroxy-2-(((2S,3S)-6-hydroxy-3-methyltetrahydro-2H-pyran-2-yl)methyl)-3,5,11-trimethyl-1-oxa-7-azaspiro[5.5]undecan-8-one	256326-85-9	C₂₁H₃₇NO₅	383.528
——	(2S,3R,4S,5S,6R,9S,11S)-2-[(2S,3S)-2,6-dihydroxy-3-methylhexyl]-9-ethyl-4-hydroxy-3,5,11-trimethyl-1-oxa-7-azaspiro[5.5]undecan-8-one	256326-86-0	C₂₁H₃₉NO₅	385.544

反应信息

作为反应物：

描述：

sanglifehrin A 在 sodium tetrahydroborate 作用下，以甲醇为溶剂，反应 3.5h，以83%的产率得到

参考文献：

名称：

Sanglifehrin−Cyclophilin Interaction: Degradation Work, Synthetic Macrocyclic Analogues, X-ray Crystal Structure, and Binding Data

摘要：

Sanglifehrin A (SFA) is a novel immunosuppressive natural product isolated from Streptomyces sp. A92-308110. SFA has a very strong affinity for cyclophilin A (IC50 = 6.9 +/- 0.9 nM) but is structurally different from cyclosporin A (CsA) and exerts its immunosuppressive activity via a novel mechanism. SFA has a complex molecular structure consisting of a 22-membered macrocycle, bearing in position 23 a nine-carbon tether terminated by a highly substituted spirobicyclic moiety. Selective oxidative cleavage of the C-26=C-27 exocyclic double bond affords the spirolactam containing fragment 1 and macrolide 2. The affinity of 2 for cyclophilin (IC50 = 29 +/- 2.1 nM) is essentially identical to SFA, which indicates that the interaction between SFA and cyclophilin A is media