(Z)-5-(2-benzyloxy-5-bromobenzylidene)-2-thioxo-thiazolidin-4-one | 796046-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-5-(2-benzyloxy-5-bromobenzylidene)-2-thioxo-thiazolidin-4-one
• 英文别名: 5-(2-benzyloxy-5-bromobenzylidene)-2-thioxo-thiazolidin-4-one；5-(2-(Benzyloxy)-5-bromobenzylidene)-2-thioxothiazolidin-4-one；(5Z)-5-[(5-bromo-2-phenylmethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 796046-85-0
• 化学式: C₁₇H₁₂BrNO₂S₂
• 分子量: 406.324
• InChiKey: XIVAQTCLHLLXCL-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-5-(2-benzyloxy-5-bromobenzylidene)-2-thioxo-thiazolidin-4-one 在 吡啶 、 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 生成 5-[(5-Bromo-2-phenylmethoxyphenyl)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of rhodanine derivatives as PRL-3 inhibitors

  摘要：

  A series of rhodanine derivatives was synthesized and evaluated for their ability to inhibit PRL-3. Benzylidene rhodanine derivative showed good biological activity, while compound 5e was the most active in this series exhibiting IC50 value of 0.9 mu M in vitro and showed a reduced invasion in cell-based assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.060
• 作为产物：
  描述：

  罗丹宁 、 2-苄氧基-5-溴苯甲醛 在 乙酸铵 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 4.0h， 以71%的产率得到(Z)-5-(2-benzyloxy-5-bromobenzylidene)-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  Rhodanine Derivatives, a Process for the Preparation Thereof and Pharmaceutical Composition Containing the Same

  摘要：

  本文披露了罗丹宁衍生物、其制备方法以及含有相同物质的药物组合物。这些罗丹宁衍生物具有对蛋白磷酸酶（PPase）如PTP1B、Prl-3、LAR、CD45、Cdc25A、Cdc25B、Cdc25C、Yop、PP1和VHR的抑制活性，并可用于预防和治疗PPase引起的疾病，包括自身免疫疾病、糖尿病、糖耐量受损、胰岛素抵抗、肥胖、癌症等，当其抑制活性被调节时。

  公开号：

  US20090042872A1

文献信息

• Rhodanine Derivatives, a Process for the Preparation Thereof and Pharmaceutical Composition Containing the Same
  申请人：Ryu Seong Eon

  公开号：US20090042872A1

  公开（公告）日：2009-02-12

  Disclosed herein are rhodanine derivatives, a method for the preparation thereof, and a pharmaceutical composition containing the same. The rhodanine derivatives have inhibitory activity against protein phosphatases (PPase) such as PTP1B, Prl-3, LAR, CD45, Cdc25A, Cdc25B, Cdc25C, Yop, PP1 and VHR, and can be applied for the prevention and treatment of PPase-caused diseases, including autoimmune diseases, diabetes, impaired glucose intolerance, insulin resistance, obesity, cancers, etc. when the inhibitory activity thereof is modulated.

  本文披露了罗丹宁衍生物、其制备方法以及含有相同物质的药物组合物。这些罗丹宁衍生物具有对蛋白磷酸酶（PPase）如PTP1B、Prl-3、LAR、CD45、Cdc25A、Cdc25B、Cdc25C、Yop、PP1和VHR的抑制活性，并可用于预防和治疗PPase引起的疾病，包括自身免疫疾病、糖尿病、糖耐量受损、胰岛素抵抗、肥胖、癌症等，当其抑制活性被调节时。
• WO2007/81091
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and biological evaluation of thiazolidine-2,4-dione and 2,4-thione derivatives as inhibitors of translation initiation
  作者：Han Chen、Yun-Hua Fan、Amarnath Natarajan、Yuhong Guo、Julia Iyasere、Fred Harbinski、Lia Luus、William Christ、Huseyin Aktas、Jose A. Halperin

  DOI：10.1016/j.bmcl.2004.08.017

  日期：2004.11

  In an effort to generate novel translation initiation inhibitors for cancer therapy, a series of 2'-benzyloxy-5'-substituted-5-benzylidene-thiazolidine-2,4-thione and dione derivatives was synthesized and evaluated for activity in translation initiation specific assays. Several candidates of the 5-benzylidene-thiazolidine-2,4-diones (3c, 3d, and 3f) and -thiones (2b, 2e, and 2j), inhibit cell growth with low muM GI(50) mediated by inhibition of translation initiation, which involves partial depletion of intracellular Ca2+ stores and strong phosphorylation of eIF2alpha. (C) 2004 Elsevier Ltd. All rights reserved.
• US8148541B2
  申请人：——

  公开号：US8148541B2

  公开（公告）日：2012-04-03
• Synthesis and biological evaluation of rhodanine derivatives as PRL-3 inhibitors
  作者：Jin Hee Ahn、Seung Jun Kim、Woul Seong Park、Sung Yun Cho、Jae Du Ha、Sung Soo Kim、Seung Kyu Kang、Dae Gwin Jeong、Suk-Kyeong Jung、Sang-Hyeup Lee、Hwan Mook Kim、Song Kyu Park、Ki Ho Lee、Chang Woo Lee、Seong Eon Ryu、Joong-Kwon Choi

  DOI：10.1016/j.bmcl.2006.02.060

  日期：2006.6

  A series of rhodanine derivatives was synthesized and evaluated for their ability to inhibit PRL-3. Benzylidene rhodanine derivative showed good biological activity, while compound 5e was the most active in this series exhibiting IC50 value of 0.9 mu M in vitro and showed a reduced invasion in cell-based assay. (c) 2006 Elsevier Ltd. All rights reserved.