4-[(1,3-苯并噻唑-2-基硫代)甲基]苯甲酸 | 82145-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 4-[(1,3-苯并噻唑-2-基硫代)甲基]苯甲酸
• 英文名称: 2-(4-Carboxybenzylthio)benzothiazole
• 英文别名: 4-[(1,3-Benzothiazol-2-ylthio)methyl]benzoic acid；4-(1,3-benzothiazol-2-ylsulfanylmethyl)benzoic acid
• CAS: 82145-84-4
• 化学式: C₁₅H₁₁NO₂S₂
• mdl: MFCD01305170
• 分子量: 301.39
• InChiKey: XAZGUJUGDDLSEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(1,3-苯并噻唑-2-基硫代)甲基]苯甲酸 在 硫酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 生成 4-((benzo[d]thiazol-2-ylthio)methyl)-N'-(2-oxoindolin-3-ylidene)benzohydrazide
  参考文献：
  名称：

  Acylhydrazone derivatives as potential anticancer agents: Synthesis, bio-evaluation and mechanism of action

  摘要：

  A series of novel acylhydrazone derivatives were designed, synthesized and evaluated for their potential cytotoxic effects against human cancer cell lines. The preliminary results indicated that some of the obtained compounds (such as 8b, 13c) exhibited good to moderate cytotoxic activities against human HepG2, Huh-7, and BCG-823 cell lines. Especially, compounds 8c and 8e presented obviously selective cytotoxic activities against Huh-7 in vitro (8c, IC50 = 7.74 +/- 2.18 mu g/mL; 8e, IC50 = 4.46 +/- 1.05 mu g/mL) compared to 5-FU (IC50 = 10.41 +/- 3.41 mu g/mL). The highly potential compounds to induce apoptosis in HepG2 cells were analyzed by flow cytometry, and the apoptotic effects of compounds 8b and 13c were further evaluated using Annexin V-FITC/propidium iodide dual staining assay. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.069
• 作为产物：
  描述：

  methyl 4-((benzo[d]thiazol-2-ylthio)methyl)benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 4-[(1,3-苯并噻唑-2-基硫代)甲基]苯甲酸
  参考文献：
  名称：

  4-(Heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs as a novel class of histone deacetylase inhibitors

  摘要：

  The synthesis and biological evaluation of a variety of 4-(heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs is described. Some of these compounds were shown to inhibit HDAC1 with IC50 values below the micromolar range, induce hyperacetylation of histones, upregulate expression of the tumor suppressor p21(WAF1/Cip1), and inhibit proliferation of human cancer cells. In addition, certain compounds of this class were active in several human tumor xenograft models in vivo. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.057

文献信息

• Heterocyclische Sulfide, Verfahren zu ihrer Herstellung und pharmazeutische Mittel, die diese Verbindungen enthalten
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0194572A1

  公开（公告）日：1986-09-17

  Heterocyclische Sulfide der allgemeinen Formel Heterocyclus-S-R, Verfahren zu ihrer Herstellung und insbesondere ihre Verwendung zur Immunstimulation, Immunrestauration und zytostatischen Behandlung, sowie pharmazeutische Mittel für diese Indikationen, die ein solches Sulfid enthalten.

  通式为 Heterocyclus-S-R 的杂环硫化物，其制备工艺，特别是其在免疫刺激、免疫增强和细胞抑制治疗中的用途，以及用于这些适应症的含有此类硫化物的药物组合物。
• US4325959A
  申请人：——

  公开号：US4325959A

  公开（公告）日：1982-04-20
• US4409227A
  申请人：——

  公开号：US4409227A

  公开（公告）日：1983-10-11
• US4762848A
  申请人：——

  公开号：US4762848A

  公开（公告）日：1988-08-09
• 4-(Heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs as a novel class of histone deacetylase inhibitors
  作者：Sylvie Fréchette、Silvana Leit、Soon Hyung Woo、Guillaume Lapointe、Guillaume Jeannotte、Oscar Moradei、Isabelle Paquin、Giliane Bouchain、Stéphane Raeppel、Frédéric Gaudette、Nancy Zhou、Arkadii Vaisburg、Marielle Fournel、Pu Theresa Yan、Marie-Claude Trachy-Bourget、Ann Kalita、Marie-France Robert、Aihua Lu、Jubrail Rahil、A. Robert MacLeod、Jeffrey M. Besterman、Zuomei Li、Daniel Delorme

  DOI：10.1016/j.bmcl.2007.12.057

  日期：2008.2

  The synthesis and biological evaluation of a variety of 4-(heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs is described. Some of these compounds were shown to inhibit HDAC1 with IC50 values below the micromolar range, induce hyperacetylation of histones, upregulate expression of the tumor suppressor p21(WAF1/Cip1), and inhibit proliferation of human cancer cells. In addition, certain compounds of this class were active in several human tumor xenograft models in vivo. (c) 2008 Elsevier Ltd. All rights reserved.