CAS: 204326-24-9; (2S,5S)-5-((((9H-Fluoren-9-yl)Methoxy)Carbonyl)Amino)-4-Oxo-1,2,4,5,6,7-Hexahydroazepino[3,2,1-Hi]Indole-2-Carboxylic Acid

该化合物是一个复杂的有机化合物,其特点是多周期结构以及各种功能组的存在,具有六氢氨基核心,有助于其循环性质和潜在的生物活动.氟乙烯甲基碳基(Fmoc)组表示,该化合物很可能用于浸泡物合成,作为氨酸的保护组.一个箱状酸功能组的出现表明,它可能表现出酸性,影响其溶性以及在不同环境中的再活动.此外,由(2S,5S)表示的立体化学核心表明原子的具体空间安排,这可能严重影响化合物的相互作用和生物功效.总体而言,该复合体的独特结构和功能组在医药化学和相关领域引起兴趣.

英文名称(2S,5S)-5-((((9H-Fluoren-9-yl)Methoxy)Carbonyl)Amino)-4-Oxo-1,2,4,5,6,7-Hexahydroazepino[3,2,1-Hi]Indole-2-Carboxylic Acid
中文名称(3S,6S)-3-((((9H-芴-9-基)甲氧基)羰基)氨基)-4-氧代-1,2,3,4,6,7-六氢氮杂环庚烷[3,2,1-hi]吲哚-6-羧酸
IUPAC名称(3S,6S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-oxo-1,2,3,4,6,7-hexahydroazepino[3,2,1-hi]indole-6-carboxylic acid
其它别名Fmoc-(2S,5S)-5-氨基-1,2,4,5,6,7-六氢氮杂环庚烷[3,2,1-Hi]吲哚-4-酮-2-羧酸; Fmoc-(2S,5S)-5-Amino-1,2,4,5,6,7-Hexahydroazepino[3,2,1-Hi]Indole-4-One-2-Carboxylic Acid
CAS编号204326-24-9
MFCD编号:MFCD00673792
分子式:C28H24N2O5分子量:468.51
产品CID: 1035782
产品分类有机原料→分子砌块→手性化合物→手性砌块

相似结构搜索
InChIKey: NHNOPJNRVODSCV-ZEQRLZLVSA-N
InChI=1S/C28H24N2O5/c31-26-23(13-12-16-6-5-7-17-14-24(27(32)33)30(26)25(16)17)29-28(34)35-15-22-20-10-3-1-8-18(20)19-9-2-4-11-21(19)22/h1-11,22-24H,12-15H2,(H,29,34)(H,32
计算化学: 氢键受体数4.0氢键供体数2.0可旋转键数4.0

相似化合物

1290040-14-0 198560-38-2 250682-47-4

MSDS等安全信息

GHS符号GHS07
警示词Warning
危险描述H302-H315-H319-H335
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

上下游产品

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 4,7-dioxo-5-(R)-(2,2,2-trifluoroacetylamino)-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-(S)-carboxylic acid methyl ester (2S,5S)-4,7-dioxo-5-(2,2,2-trifluoroacetylamino)-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-carboxylic acid methyl ester 28H33N4O8PC28H33N4O8P 29H33F2N4O7PC29H33F2N4O7P pβMCinn-Haic-Gln-NHBn

合成工艺路线路线简述

📜9-芴甲基-N-琥珀酰亚胺基碳酸酯,Methyl (2S,11S)-9,12-Dioxo-11-(2,2,2-Trifluoroacetamido)-1-Azatricyclo[6.4.1.0λ[4,13]]Trideca-4,6,8(13)-Triene-2-Carboxylate置于palladium 10% On Activated Carbon,氢气,Lithium Hydroxide体系中,化学反应生成(2S,5S)-5-[[(9H-芴-9-基甲氧基)羰基]氨基]-1,2,4,5,6,7-六氢-4-氧代-氮杂卓并[3,2,1-Hi]吲哚-2-羧酸
参考文献:Conformationally Constrained Peptidomimetic Inhibitors Of Signal Transducer And Activator Of Transcription 3: Evaluation And Molecular Modeling
标题:Conformationally Constrained Peptidomimetic Inhibitors Of Signal Transducer And Activator Of Transcription 3: Evaluation And Molecular Modeling
摘要:Signal Transducer And Activator Of Transcription 3 (Stat3) Is Involved In Aberrant Growth And Survival Signals In Malignant Tumor Cells And Is A Validated Target For Anticancer Drug Design. We Are Targeting Its Sh2 Domain To Prevent Docking To Cytokine And Growth Factor Receptors And Subsequent Signaling. The Amino Acids Of Our Lead Phosphopeptide,Ac-Ptyr-Leu-Pro-Gln-Thr-Val-Nh2,Were Replaced With Conformationally Constrained Mimics. Structure-Affinity Studies Led To The Peptidomimetic,Pcinn-Haic-Gln-Nhbn (21). Which Had An Ic50 Of 162 Nm (Fluorescence Polarization),Compared To 290 Nm For The Lead Phosphopeptide (Pcinn = 4-Phosphoryloxycinnamate,Haic = (2S,5S)-5-Amino-1,2,4,5,6,7-Hexahydro-4-Oxo-Azepino[3,2,1-Hi]Indole-2-Carboxylic Acid). Pcinn-Haic-Gln-Oh Was Docked To The Sh2 Domain (Autodock),And The Two Highest Populated Clusters Were Subjected To Molecular Dynamics Simulations. Both Converged To A Common Peptide Conformation. The Complex Exhibits Unique Hydrogen Bonding Between Haic And Gln And Stat3 As Well As Hydrophobic Interactions Between The Protein And Pcinn And Haic.
Doi:10.1021/jm801491W