(3S,6S,8aS)-5-oxo-6-(phenylmethoxycarbonylamino)-2,3,6,7,8,8a-hexahydro-1H-indolizine-3-carboxylic acid | 158568-48-0

• 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
• 英文名称: (3S,6S,8aS)-5-oxo-6-(phenylmethoxycarbonylamino)-2,3,6,7,8,8a-hexahydro-1H-indolizine-3-carboxylic acid
• CAS: 158568-48-0
• 化学式: C₁₇H₂₀N₂O₅
• 分子量: 332.356
• InChiKey: NCYSYPYCBYUTRD-IHRRRGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,6S,8aS)-5-oxo-6-(phenylmethoxycarbonylamino)-2,3,6,7,8,8a-hexahydro-1H-indolizine-3-carboxylic acid 在 聚合甲醛 、 1-羟基苯并三唑 、 溶剂黄146 、 苯甲醚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(3S,6S,8aS)-3-((S)-2-Hydroxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-5-oxo-octahydro-indolizin-6-yl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Conformationally constrained inhibitors of caspase-1 (interleukin-1β converting enzyme) and of the human ced-3 homologue caspase-3 (CPP32, apopain)

  摘要：

  A systematic study of interleukin-lp converting enzyme (ICE, caspase-1) and caspase-3 (CPP32, apopain) inhibitors incorporating a PGammaP3 conformationally constrained dipeptide mimetic is reported. Depending on the nature of the P-4 substituent, highly selective inhibitors of both Csp-l or Csp-3 were obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00498-3
• 作为产物：
  描述：

  氯甲酸苄酯 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 (3S,6S,8aS)-5-oxo-6-(phenylmethoxycarbonylamino)-2,3,6,7,8,8a-hexahydro-1H-indolizine-3-carboxylic acid
  参考文献：
  名称：

  合成6,5-稠合双环内酰胺作为潜在的二肽β-turn模拟物

  摘要：

  使用Schoellkopf双内酯醚方法，对二肽模拟物（3 S，6 S，9 S）-6-氨基-5-氧代吲哚并咪唑-3-羧酸1及其Z保护的衍生物9的首次简短合成进行了描述，然后进行高度特异性的分子内还原胺化和自发内酰胺化。这些6，5-稠合的双环内酰胺可被视为构象受限的丙氨酰基-脯氨酸β-转角模拟物。

  DOI：

  10.1016/s0040-4039(00)73120-0

文献信息

• HEPATITIS C VIRUS INHIBITORS
  申请人：Or Yat Sun

  公开号：US20110008288A1

  公开（公告）日：2011-01-13

  The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit RNA-containing virus, particularly the hepatitis C virus (HCV). Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.
• US8609648B2
  申请人：——

  公开号：US8609648B2

  公开（公告）日：2013-12-17
• Conformationally constrained inhibitors of caspase-1 (interleukin-1β converting enzyme) and of the human ced-3 homologue caspase-3 (CPP32, apopain)
  作者：Donald S. Karanewsky、Xu Bai、Steven D. Linton、Joseph F. Krebs、Joe Wu、Bryan Pham、Kevin J. Tomaselli

  DOI：10.1016/s0960-894x(98)00498-3

  日期：1998.10

  A systematic study of interleukin-lp converting enzyme (ICE, caspase-1) and caspase-3 (CPP32, apopain) inhibitors incorporating a PGammaP3 conformationally constrained dipeptide mimetic is reported. Depending on the nature of the P-4 substituent, highly selective inhibitors of both Csp-l or Csp-3 were obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of 6,5-fused bicyclic lactams as potential dipeptide β-turn mimetics
  作者：Rudolf Mueller、Laszlo Revesz

  DOI：10.1016/s0040-4039(00)73120-0

  日期：1994.6

  The first short synthesis of the dipeptide mimetic (3S, 6S, 9S)-6-amino-5-oxoindolizidine-3-carboxylic acid 1 and its Z-protected derivative 9 is described, employing the Schoellkopf bislactim-ether methodology, followed by a highly specific intramolecular reductive amination and spontaneous lactamization. These 6,5-fused bicyclic lactams may be viewed as conformationally restricted alanyl-proline

  使用Schoellkopf双内酯醚方法，对二肽模拟物（3 S，6 S，9 S）-6-氨基-5-氧代吲哚并咪唑-3-羧酸1及其Z保护的衍生物9的首次简短合成进行了描述，然后进行高度特异性的分子内还原胺化和自发内酰胺化。这些6，5-稠合的双环内酰胺可被视为构象受限的丙氨酰基-脯氨酸β-转角模拟物。