氨甲酸,[(3S)-四氢-5-羰基-2-(苯基甲氧基)-3-呋喃基]-,2-丙烯基酯 | 192753-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 氨甲酸,[(3S)-四氢-5-羰基-2-(苯基甲氧基)-3-呋喃基]-,2-丙烯基酯
• 英文名称: (3S)-(2-benzyloxy-5-oxo-tetrahydrofuran-3-yl)carbamic acid allyl ester
• 英文别名: (2RS,3S)-3-allyloxycarbonylamino-2-benzyloxy-5-oxotetrahydrofuran；N-allyloxycarbonyl-4-amino-5-benzyloxy-2-oxotetrahydrofuran；(3S,2RS) 3-allyloxycarbonylamino-2-benzyloxy-5-oxotetrahydrofuran；(3S,2RS)3-allyloxycarbonylamino-2-benzyloxy-5-oxotetrahydrofuran；prop-2-enyl N-[(3S)-5-oxo-2-phenylmethoxyoxolan-3-yl]carbamate
• CAS: 192753-30-3
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: ZEZKRQQOECKKCQ-NBFOIZRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氨甲酸,[(3S)-四氢-5-羰基-2-(苯基甲氧基)-3-呋喃基]-,2-丙烯基酯 在 bis-triphenylphosphine-palladium(II) chloride 、 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-4-Amino-5-benzyloxy-dihydro-furan-2-one
  参考文献：
  名称：

  caspase-3的有效和选择性拟肽抑制剂的设计与合成。

  摘要：

  在本文中，我们报告了新型有效且选择性的caspase-3抑制剂的合成和表征，caspase-3是半胱氨酸蛋白酶caspase家族的成员，在许多人类疾病中起着重要作用。该分子代表3（S）-乙酰氨基-N- [1-[（（（（3S）-2-hydroxy-5-oxo-tetrahydrofuran-3-yl）carbamoyl）methyl] -2-oxo-5-phenyl- 2,3-二氢-1H-苯并[e] [1,4]二氮杂pin-3-基]琥珀酸，四肽Ac-DEVD-H的单环构象受约束形式，其中1,4-苯并二氮杂核为在肽序列内部引入。

  DOI：

  10.1021/jm049248f
• 作为产物：
  描述：

  (S)-3-allyloxycarbonylamino-4-hydroxy-butyric acid tert-butyl ester 在 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.42h， 生成 氨甲酸,[(3S)-四氢-5-羰基-2-(苯基甲氧基)-3-呋喃基]-,2-丙烯基酯
  参考文献：
  名称：

  caspase-3的有效和选择性拟肽抑制剂的设计与合成。

  摘要：

  在本文中，我们报告了新型有效且选择性的caspase-3抑制剂的合成和表征，caspase-3是半胱氨酸蛋白酶caspase家族的成员，在许多人类疾病中起着重要作用。该分子代表3（S）-乙酰氨基-N- [1-[（（（（3S）-2-hydroxy-5-oxo-tetrahydrofuran-3-yl）carbamoyl）methyl] -2-oxo-5-phenyl- 2,3-二氢-1H-苯并[e] [1,4]二氮杂pin-3-基]琥珀酸，四肽Ac-DEVD-H的单环构象受约束形式，其中1,4-苯并二氮杂核为在肽序列内部引入。

  DOI：

  10.1021/jm049248f

文献信息

• Inhibitors of interleukin-1beta converting enzyme
  申请人：Batchelor James Mark

  公开号：US20050143436A1

  公开（公告）日：2005-06-30

  The present invention relates to novel classes of compounds which are inhibitors of interleukin-1β converting enzyme. The ICE inhibitors of this invention are characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting ICE activity and consequently, may be advantageously used as agents against IL-1-, apoptosis-, IGIF-, and IFN-γ-mediated diseases, inflammatory diseases, autoimmune diseases, destructive bone disorders, proliferative disorders, infectious diseases, degenerative diseases, and necrotic diseases. This invention also relates to methods for inhibiting ICE activity, for treating interleukin-1-, apoptosis-, IGIF- and IFN-γ-mediated diseases and decreasing IGIF and IFN-γ production using the compounds and compositions of this invention. This invention also relates to methods for preparing N-acylamino compounds.

  本发明涉及一类新型化合物，这些化合物是白细胞介素-1β转化酶的抑制剂。本发明的ICE抑制剂具有特定的结构和理化特征。本发明还涉及包含这些化合物的药物组合物。本发明的化合物和药物组合物特别适用于抑制ICE活性，因此可以有利地用作对抗IL-1、凋亡、IGIF和IFN-γ介导的疾病、炎症性疾病、自身免疫疾病、破坏性骨疾病、增生性疾病、传染性疾病、退行性疾病和坏死性疾病的药剂。本发明还涉及抑制ICE活性的方法，用于治疗白细胞介素-1、凋亡、IGIF和IFN-γ介导的疾病，以及使用本发明的化合物和组合物减少IGIF和IFN-γ的产生的方法。本发明还涉及制备N-酰氨基化合物的方法。
• Caspase inhibitors and uses thereof
  申请人：——

  公开号：US20030232846A1

  公开（公告）日：2003-12-18

  This invention provides novel compounds, and pharmaceutically acceptable derivatives thereof, that are useful as caspase inhibitors. These compounds have the general formula I: 1 where R 1 , R 2 , and R 3 are as described herein, Ring A contains zero to two double bonds, each X is independently selected from nitrogen or carbon, at least one X in Ring A is a nitrogen, Ring A is optionally substituted as described, and may be fused to a saturated or unsaturated five to seven membered ring containing zero to three heteroatoms, and provided that when X 3 is a carbon, a substituent on X 3 is attached by an atom other than nitrogen.

  这项发明提供了新颖的化合物及其药用可接受的衍生物，其作为caspase抑制剂有用。这些化合物具有一般式I：其中R1、R2和R3如本文所述，环A含有零至两个双键，每个X独立地选自氮或碳，环A中至少一个X是氮，环A如所述可被取代，且可与含有零至三个杂原子的饱和或不饱和的五至七元环融合，且当X3为碳时，X3上的取代基由非氮原子连接。
• Inhibitors of interleukin-1&bgr; converting enzyme
  申请人：Vertex Pharmaceutical, Inc.

  公开号：US06350741B1

  公开（公告）日：2002-02-26

  The present invention relates to novel classes of compounds which are inhibitors of interleukin-1&bgr; converting enzyme (“ICE”). This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting ICE activity and consequently, may be advantageously used as agents against interleukin-1-(“IL-1”), apoptosis-, interferon-&ggr; inducing factor-(IGIF), or interferon-&ggr;-(“IFN-&ggr;”) mediated diseases, including inflammatory diseases, autoimmune diseases, destructive bone disorders, proliferative disorders, infectious diseases, and degenerative diseases. This invention also relates to methods for inhibiting ICE activity and decreasing IGIF production and IFN-&ggr; production and methods for treating interleukin-1, apoptosis- and interferon-&ggr;-mediated diseases using the compounds and compositions of this invention. This invention also relates to methods of preparing the compounds of this invention.

  本发明涉及一种新的化合物类别，它们是白细胞介素-1β转化酶（“ICE”）的抑制剂。本发明还涉及包含这些化合物的药物组合物。本发明的化合物和药物组合物特别适用于抑制ICE活性，因此可以优势地用作对白细胞介素-1（“IL-1”）、凋亡、干扰素-γ诱导因子（“IGIF”）或干扰素-γ（“IFN-γ”）介导疾病的治疗剂，包括炎症性疾病、自身免疫性疾病、破坏性骨疾病、增生性疾病、感染性疾病和退行性疾病。本发明还涉及通过使用本发明的化合物和组合物来抑制ICE活性并减少IGIF产生和IFN-γ产生的方法，以及用于治疗白细胞介素-1、凋亡和干扰素-γ介导的疾病的方法。本发明还涉及制备本发明的化合物的方法。
• Inhibitors of interleukin-1.beta. converting enzyme
  申请人：Vertex Pharmaceuticals, Inc.

  公开号：US05656627A1

  公开（公告）日：1997-08-12

  The present invention relates to novel classes of compounds which are inhibitors of interleukin-1.beta. converting enzyme. The ICE inhibitors of this invention are characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting ICE activity and consequently, may be advantageously used as agents against interleukin-1 mediated diseases, including inflammatory diseases, autoimmune diseases and neurodegenerative diseases. This invention also relates to methods for inhibiting ICE activity and methods for treating interleukin-1 mediated diseases using the compounds and compositions of this invention.

  本发明涉及一种新的化合物类别，其为白细胞介素-1β转化酶的抑制剂。本发明的ICE抑制剂具有特定的结构和物理化学特征。本发明还涉及包含这些化合物的制药组合物。本发明的化合物和制药组合物特别适用于抑制ICE活性，因此可以作为对白细胞介素-1介导的疾病，包括炎症性疾病、自身免疫性疾病和神经退行性疾病的药物代理。本发明还涉及使用本发明的化合物和组合物抑制ICE活性和治疗白细胞介素-1介导的疾病的方法。
• Inhibitors of interleukin-1 beta converting enzyme
  申请人：Bemis W. Guy

  公开号：US20080070953A1

  公开（公告）日：2008-03-20

  The present invention relates to novel classes of compounds which are inhibitors of interleukin-1β converting enzyme. The ICE inhibitors of this invention are characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting ICE activity and consequently, may be advantageously used as agents against interleukin-1 mediated diseases, including inflammatory diseases, autoimmune diseases and neurodegenerative diseases. This invention also relates to methods for inhibiting ICE activity and methods for treating interleukin-1 mediated diseases using the compounds and compositions of this invention.

  本发明涉及一种新型的化合物类别，它们是白细胞介素-1β转化酶的抑制剂。本发明的ICE抑制剂具有特定的结构和物理化学特征。本发明还涉及包含这些化合物的制药组合物。本发明的化合物和制药组合物特别适用于抑制ICE活性，因此可以作为对白细胞介素-1介导的疾病，包括炎症性疾病、自身免疫性疾病和神经退行性疾病的治疗药物。本发明还涉及使用本发明的化合物和组合物抑制ICE活性的方法以及治疗白细胞介素-1介导的疾病的方法。