(Z)-3-amino-5-benzylidene-2-thioxothiazolidin-4-one | 160757-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-3-amino-5-benzylidene-2-thioxothiazolidin-4-one
• 英文别名: 3-Amino-5-benzyliden-2-thioxo-thiazolidin-4-on；(5Z)-3-amino-5-benzylidene-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 160757-27-7
• 化学式: C₁₀H₈N₂OS₂
• 分子量: 236.318
• InChiKey: RADJDINPADSTBJ-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-bromo-3,3-diethoxypropionate 、 (Z)-3-amino-5-benzylidene-2-thioxothiazolidin-4-one 以 甲苯 为溶剂， 反应 2.0h， 以47%的产率得到ethyl (2Z)-2-benzylidene-3-oxopyrazolo[5,1-b][1,3]thiazole-7-carboxylate
  参考文献：
  名称：

  串联缩合硫挤出反应合成2,3-二氢吡唑并[5,1- b ]噻唑

  摘要：

  2,3-二氢吡[5,1- b ]噻唑类3是杂环系统的第一代表，其可方便地通过加热制备的3- aminorhodanines 1与2-溴-3,3- diethoxypropionate（2），经由一串联缩合-硫挤出反应。

  DOI：

  10.1002/jhet.5570310675
• 作为产物：
  描述：

  N-氨基绕丹宁 、 苯甲醛 在 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 0.42h， 以60%的产率得到(Z)-3-amino-5-benzylidene-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  SAR and Mode of Action of Novel Non-Nucleoside Inhibitors of Hepatitis C NS5b RNA Polymerase

  摘要：

  Novel non-nucleoside inhibitors of the HCV RNA polymerase (NS5b) with sub-micromolar biochemical potency have been identified which are selective for the inhibition of HCV NS5b over other polymerases. The structures of the complexes formed between several of these inhibitors and HCV NS5b were determined by X-ray crystallography, and the inhibitors were found to bind in an allosteric binding site separate from the active site. Structure-activity relationships and structural studies have identified the mechanism of action for compounds in this series, several of which possess drug-like properties, as unique, reversible, covalent inhibitors of HCV NS5b.

  DOI：

  10.1021/jm050859x

文献信息

• Regioselektive Kondensationen sowieN-Acylierungen an 3-Aminorhodaninen
  作者：Wolfgang Hanefeld、Martin Schlitzer

  DOI：10.1002/ardp.19933261109

  日期：——

  3‐Aminorhodanin wurde regioselektiv an der 3‐Amino‐ oder der 5‐Methylengruppe mit Aldehyden kondensiert. Mit Carbonsäurechloriden oder ‐anhydriden gelingt die Acylierung der 3‐Aminofunktion.

  3-氨基若丹宁与醛在3-氨基或5-亚甲基上进行区域选择性缩合。3-氨基官能团可以用羧酸氯化物或酸酐进行酰化。
• NS5B HCV polymerase inhibitors
  申请人：Tularik Inc.

  公开号：US20020142290A1

  公开（公告）日：2002-10-03

  Compounds, compositions and methods are provided that are useful in the treatment and prevention of certain viral infections and associated diseases. In particular, the compounds of the invention inhibit the activity of a viral RNA polymerase. The subject methods are particularly useful in the treatment of diseases causes by hepatitis C virus infection.

  提供了一些在治疗和预防特定病毒感染和相关疾病中有用的化合物、组合物和方法。具体来说，本发明的化合物抑制了病毒RNA聚合酶的活性。这些方法特别适用于治疗由丙型肝炎病毒感染引起的疾病。
• Exploration of inhibitors for diaminopimelate aminotransferase
  作者：Chenguang Fan、Matthew D. Clay、Michael K. Deyholos、John C. Vederas

  DOI：10.1016/j.bmc.2010.02.001

  日期：2010.3

  Bacteria and higher plants make L-lysine from diaminopimelic acid (DAP). In mammals L-lysine is an essential amino acid that must be acquired from the diet as the biosynthetic pathway is absent for this key constituent of proteins. Recently, LL-diaminopimelate aminotransferase (LL-DAP-AT), a pyridoxal-5'-phosphate (PLP)-dependent enzyme, was reported to catalyze a key step in the route to L-lysine in plants and Chlamydia. Specific inhibitors of this enzyme could thus potentially serve as herbicides or antibiotics that are non-toxic to mammals. In this work, 29,201 inhibitors were screened against LL-DAP-AT and the IC50 values were determined for the top 46 compounds. An aryl hydrazide and rhodanine derivatives were further modified to generate 20 analogues that were also tested against LL-DAP-AT. These analogues provide additional structure-activity relationships (SAR) that are useful in guiding further design of inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.
• Hanefeld Wolfgang, Schlitzer Martin, Arch. Pharm, 326 (1993) N 11, S 887-891
  作者：Hanefeld Wolfgang, Schlitzer Martin

  DOI：——

  日期：——
• US6727267B2
  申请人：——

  公开号：US6727267B2

  公开（公告）日：2004-04-27