methyl 4-((benzo[d]thiazol-2-ylthio)methyl)benzoate | 315239-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-((benzo[d]thiazol-2-ylthio)methyl)benzoate
• 英文别名: Methyl 4-[(1,3-benzothiazol-2-ylsulfanyl)methyl]benzoate；methyl 4-(1,3-benzothiazol-2-ylsulfanylmethyl)benzoate
• CAS: 315239-25-9
• 化学式: C₁₆H₁₃NO₂S₂
• 分子量: 315.417
• InChiKey: KOZOGTICWSMJFV-UHFFFAOYSA-N

物化性质

• 沸点：
  485.7±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  92.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  对氯甲基苯甲酸 在 硫酸 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 methyl 4-((benzo[d]thiazol-2-ylthio)methyl)benzoate
  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

文献信息

• Three‐Component Synthesis of 2‐Substituted Thiobenzoazoles Using Tetramethyl Thiuram Monosulfide (TMTM) as Thiocarbonyl Surrogate
  作者：Xi Wang、Chun‐Yan Wu、Yue‐Sheng Li、Zhi‐Bing Dong

  DOI：10.1002/ejoc.202001214

  日期：2020.11.22

  A metal‐free synthesis of 2‐benzyl/allyl‐substituted thiobenzoazoles was developed starting from tetramethyl thiuram monosulfide (TMTM) which served as thiocarbonyl surrogate. By using 2‐aminophenols (or 2‐aminothiophenols, or 1,2‐phenylenediamines) and TMTM as starting materials, 2‐mercaptobenzoazoles could be synthesized efficiently, and the subsequent C–S bond formation with allyl/benzyl halides

  从用作硫代羰基替代物的四甲基秋兰姆单硫化物（TMTM）出发，开发了2-苄基/烯丙基取代的硫代苯并恶唑的无金属合成方法。通过使用2-氨基苯酚（或2-氨基硫酚或1,2-苯二胺）和TMTM作为起始原料，可以高效合成2-巯基苯并恶唑，随后与烯丙基/苄基卤化物的CS键形成最终产物（ 2-烯丙基/苄基取代的硫代苯并唑），具有良好或优异的收率。
• One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water
  作者：Shi-Bo Zhang、Xing Liu、Ming-Yuan Gao、Zhi-Bing Dong

  DOI：10.1021/acs.joc.8b02136

  日期：2018.12.21

  A transition-metal-free protocol for the one-pot synthesis of 2-benzyl/2-allyl-substituted thiobenzoazoles in water was developed. The cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) gave mercapto benzoheterocycles, and the subsequent C-S coupling with benzyl or allyl halides furnished the desired products in good to excellent yields. This method features transition-metal-free conditions with water as a solvent, an easy performance, mild reaction conditions, a wide substrate scope, and good to excellent yields, thus paving an efficient and useful way to establish a library of potentially active drug molecules.
• 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.
• Acylhydrazone derivatives as potential anticancer agents: Synthesis, bio-evaluation and mechanism of action
  作者：Xifang Yu、Liqiao Shi、Shaoyong Ke

  DOI：10.1016/j.bmcl.2015.10.069

  日期：2015.12

  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.