2-[(5Z)-5-(4-bromobenzylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methylbutanoic acid | 1122565-91-6

• 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: 2-[(5Z)-5-(4-bromobenzylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methylbutanoic acid
• 英文别名: 2-[(5Z)-5-[(4-bromophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methylbutanoic acid
• CAS: 1122565-91-6
• 化学式: C₁₅H₁₄BrNO₃S₂
• 分子量: 400.317
• InChiKey: COHIEJLWRGREHV-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(5Z)-5-(4-bromobenzylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methylbutanoic acid 在 氯化亚砜 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 0.17h， 生成 2-[(5Z)-5-(4-bromobenzylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methyl-N-[2-(morpholin-4-yl)ethyl]butanamide
  参考文献：
  名称：

  Synthesis, Physicochemical Properties, Drug Likeness, and Antitumor Activity of 2-[5-(4-Bromobenzylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methylbutanoic Acid Esters and Amides

  摘要：

  DOI：

  10.1134/s1070428021010048
• 作为产物：
  描述：

  3-methyl-2-(4-oxo-2-thioxothiazolidin-3-yl)butanoic acid 、 对溴苯甲醛 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以94%的产率得到2-[(5Z)-5-(4-bromobenzylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methylbutanoic acid
  参考文献：
  名称：

  Synthesis, Physicochemical Properties, Drug Likeness, and Antitumor Activity of 2-[5-(4-Bromobenzylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methylbutanoic Acid Esters and Amides

  摘要：

  DOI：

  10.1134/s1070428021010048

文献信息

• Small molecule inhibitors targeted at Bcl-2
  申请人：Wang Shaomeng

  公开号：US20080058322A1

  公开（公告）日：2008-03-06

  The present invention relates to small molecule antagonists of Bcl-2 family proteins such as Bcl-2 and/or Bcl-X L . In particular, the present invention provides non-peptide cell permeable small molecules (e.g., tricyclo-dibenzo-diazocine-dioxides) that bind to a pocket in Bcl-2/Bcl-X L that block the anti-apoptotic function of these proteins in cancer cells and tumor tissues exhibiting Bcl-2 protein overexpression. In preferred embodiments, the small molecules of the present invention are active at the BH3 binding pocket of Bcl-2 family proteins (e.g., Bcl-2, Bcl-X L , and Mcl-1). The compositions and methods of the present invention are useful therapeutics for cancerous diseases either alone or in combination with chemotherapeutic or other drugs.

  本发明涉及Bcl-2家族蛋白（如Bcl-2和/或Bcl-XL）的小分子拮抗剂。特别地，本发明提供了非肽细胞渗透小分子（例如三环二苯并二氮杂环二氧化物），它们结合到Bcl-2/Bcl-XL的一个口袋，阻止这些蛋白在表达Bcl-2蛋白的癌细胞和肿瘤组织中的抗凋亡功能。在优选实施例中，本发明的小分子在Bcl-2家族蛋白的BH3结合口袋（例如Bcl-2、Bcl-XL和Mcl-1）中活性。本发明的组合物和方法可用于治疗癌症疾病，可以单独使用或与化疗或其他药物联合使用。
• Inhibitors of BCL-2
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US10058588B2

  公开（公告）日：2018-08-28

  A protease resistant polypeptide includes an amino acid sequence that has a sequence identity at least 80% homologous to about 10 to 80 consecutive amino acids of SEQ ID NO:1.

  抗蛋白酶多肽包括与 SEQ ID NO:1 的约 10 至 80 个连续氨基酸具有至少 80% 同源性的氨基酸序列。
• Synthetic lethality in cancer
  申请人：The Governors of the University of Alberta

  公开号：US10087448B2

  公开（公告）日：2018-10-02

  There is described herein compounds, compositions and methods for inducing synthetic lethality in a cancer cell(s).

  本文描述了诱导癌细胞合成致死的化合物、组合物和方法。
• Inhibitors of Bcl-2
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US11229641B2

  公开（公告）日：2022-01-25

  Compounds and pharmaceutical compositions thereof for inducing apoptosis in a cell expressing Bcl-2 and IP3R and their use in a method for treating neoplastic disorders in a subject.

  用于诱导表达 Bcl-2 和 IP3R 的细胞凋亡的化合物及其药物组合物，以及它们在治疗受试者肿瘤性疾病的方法中的用途。
• Method for controlling the yeast-to-filamentous growth transition in fungi
  申请人：Toenjes Kurt A.

  公开号：US20090018173A1

  公开（公告）日：2009-01-15

  A method for controlling yeast-to-filamentous growth transition in fungi comprising contacting a fungal cell with an anti-fungal small molecule in an amount effective to reduce or inhibit the yeast-to-filamentous growth transition, wherein the anti-fungal small molecule is 5-(p-Bromobenzylidine)-α-isopropyl-4-oxo-2-thioxo-3-thiozolidineacetic acid or an analog thereof. A method for treating fungal infections comprising contacting one or more fungal cells with an anti-fungal small molecule in an amount effective to control the fungal infection, wherein the anti-fungal small molecule is 5-(p-Bromobenzylidine)-α-isopropyl-4-oxo-2-thioxo-3-thiozolidineactic acid or an analog thereof.