(3S)-N-CBZ-3-氨基-2-羰基吡咯 | 118507-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3S)-N-CBZ-3-氨基-2-羰基吡咯
• 英文名称: (3S)-3-benzyloxycarbonylamino-2-pyrrolidinone
• 英文别名: (S)-3-benzyloxycarbonylamino-2-pyrrolidinone；(S)-benzyl (2-oxopyrrolidin-3-yl)carbamate；benzyl (S)-(2-oxopyrrolidin-3-yl)carbamate；((S)-2-oxo-pyrrolidin-3-yl)-carbamic acid benzyl ester；((S)-2-Oxo-pyrrolidin-3-yl)-carbamidsaeure-benzylester；N-((3S)-2-Oxopyrrolidin-3-yl)(phenylmethoxy)carboxamide；benzyl N-[(3S)-2-oxopyrrolidin-3-yl]carbamate
• CAS: 118507-50-9
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: DAMJCWMGELCIMI-JTQLQIEISA-N

物化性质

• 熔点：
  179-181 °C
• 沸点：
  496.2±44.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H317
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  (3S)-N-CBZ-3-氨基-2-羰基吡咯 在 正丁基锂 、 氨 、 三氯氧磷 作用下， 以 正己烷 为溶剂， 生成 (3S)-3-benzyloxycarbonylamino-1-diaminophosphoryl-2-pyrrolidinone
  参考文献：
  名称：

  Synthesis and biological activity of sulphostin analogues, novel dipeptidyl peptidase IV inhibitors

  摘要：

  The structure of sulphostin (1). a novel dipeptidyl peptidase IV (DPP-IV) inhibitor, is consisted of three key functional groups, including a characteristic amino(sulfoamino)phosphinyl group, on a piperidine ring. To examine the relationship between its structure and the inhibitory activity against DPP-IV. various analogues were synthesized and their activities were investitlaied- These results indicated that all of the functional groups on the piperidine ring were crucial to the DPP-IV inhibitory activity of sulphostin. and that the sulfonic acid group, which constructed the amino(sulfoamino)phosphinyl group, contributed to the stability of the compound. Moreover, those functional groups should be adjoined on the piperidine ring for the inhibitory acivity. The size of the nitrogen-containing heterocyclic ring including piperidine appeared to scarcely affect the activity. In the present study, the sulfonic acid-deficient five-membered ring analogue 27a showed the strongest inhibitory activity (IC50 = 11 nM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.036
• 作为产物：
  描述：

  N-alpha-苄氧羰基-L-2,4-二氨基丁酸 在 4-二甲氨基吡啶 、 二苯基硅烷 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 42.0h， 以78%的产率得到(3S)-N-CBZ-3-氨基-2-羰基吡咯
  参考文献：
  名称：

  二苯基硅烷作为酰胺键形成的偶联剂

  摘要：

  描述了使用二苯基硅烷作为偶联剂形成酰胺键的简单程序。这种方法可以使羧酸与伯胺和仲胺直接偶联，仅释放出氢和作为副产物的硅氧烷。每个合作伙伴只需要一个等价物，即可提供一种可持续性更高的酰胺化方法，从而减少浪费。通过添加Hünig碱（DIPEA）和4-二甲基氨基吡啶（DMAP），该方法还扩展到肽和内酰胺的合成。

  DOI：

  10.1039/c7gc02643a

文献信息

• [EN] SULPHONYLAMINOPYRROLIDINONE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION<br/>[FR] DÉRIVÉS SULFONYLAMINOPYRROLIDINONE, PRÉPARATION ET APPLICATION THÉRAPEUTIQUE DE CEUX-CI
  申请人：SANOFI SA

  公开号：WO2013092756A1

  公开（公告）日：2013-06-27

  The invention relates to new sulphonylaminopyrrolidinone compounds having antithrombotic activity which, in particular, inhibit blood clotting factor IXa and/ or factor Xa, to processes for their preparation and to use thereof as drugs.

  这项发明涉及具有抗血栓活性的新磺胺基吡咯烷酮化合物，特别是抑制凝血因子IXa和/或Xa，以及它们的制备方法和作为药物的用途。
• Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors
  申请人：——

  公开号：US20040006062A1

  公开（公告）日：2004-01-08

  The present application describes sulfonylaminovalerolactams and derivatives thereof of Formula I: 1 or pharmaceutically acceptable salt forms thereof, wherein ring G is a mono- or bicyclic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了Formula I中的磺酰氨基戊内内酰胺及其衍生物，或其药用盐形式，其中环G是单环或双环碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶抑制剂，特别是对凝血因子Xa的抑制剂。
• Synthesis and in vitro enzyme activity of aza, oxa and thia derivatives of bacterial cell wall biosynthesis intermediates†
  作者：Russell J. Cox、Paul S. H. Wang

  DOI：10.1039/b105117m

  日期：——

  Mechanism based inhibitors of diaminopimelate aminotransferase (DAP-AT) were designed using knowledge of its substrate specificity and mechanism. Synthesis of thiolester and amide substrate analogues was achieved prior to in vitro inhibition studies, but ester analogues proved too unstable to isolate. Thia substrate analogues showed no inhibitory properties, but the aza substrate analogue 12a showed reversible inhibition vs. DAP-AT and time dependent inhibition in the absence of the natural substrate 4. Substrate analogue 12a is the first example of an amide inhibitor of PLP dependent enzymes. Antibiotic properties of 12a were also briefly assessed.

  基于对二氨基庚二酸转氨酶（DAP-AT）的底物特异性及作用机制的了解，设计了机制型抑制剂。在体外抑制实验之前，成功合成了硫酯及酰胺类底物类似物，但酯类类似物过于不稳定，无法分离。硫类底物类似物未表现出抑制作用，但氮类底物类似物12a对DAP-AT显示出可逆抑制性，并且在缺乏天然底物4的情况下显示出时间依赖性抑制作用。底物类似物12a是首个PLP依赖性酶的酰胺类抑制剂示例。同时，也对12a的抗菌特性进行了简要评估。
• Sulfonic acid sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US06281227B1

  公开（公告）日：2001-08-28

  The compounds of formula I herein exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, for treating a patient suffering from, or subject to, a physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.

  本文中的化合物具有有用的药理活性，因此被纳入药物组合物中，并用于治疗患有某些医学疾病的患者。更具体地说，它们是凝血因子Xa活性的抑制剂。本发明涉及具有I式化合物的化合物、含有I式化合物的组合物，以及它们的用途，用于治疗患有或受到生理状况影响的患者，这些生理状况可以通过给予凝血因子Xa活性抑制剂来改善。
• Total synthesis of padanamides A and B
  作者：Bohua Long、Shoubin Tang、Ligong Chen、Shiwei Qu、Bo Chen、Junyang Liu、Anita R. Maguire、Zhuo Wang、Yuqing Liu、Hui Zhang、Zhengshuang Xu、Tao Ye

  DOI：10.1039/c3cc00178d

  日期：——

  The first total syntheses of padanamides A and B have been achieved, unambiguously confirming their structures.

  首次完成了padanamides A和B的全合成，明确确认了它们的结构。