4-{6-[(pyridin-3-ylmethyl)-amino]-benzothiazol-2-ylsulfanylmethyl}-benzoic acid methyl ester

• 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: 4-{6-[(pyridin-3-ylmethyl)-amino]-benzothiazol-2-ylsulfanylmethyl}-benzoic acid methyl ester
• 英文别名: Methyl 4-[[6-(pyridin-3-ylmethylamino)-1,3-benzothiazol-2-yl]sulfanylmethyl]benzoate
• 化学式: C₂₂H₁₉N₃O₂S₂
• 分子量: 421.544
• InChiKey: APMDWGGBOHTSTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-{6-[(pyridin-3-ylmethyl)-amino]-benzothiazol-2-ylsulfanylmethyl}-benzoic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成
  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：

  3-溴甲基吡啶 、 4-(6-Amino-benzothiazol-2-ylsulfanylmethyl)-benzoic acid methyl ester 在 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 生成 4-{6-[(pyridin-3-ylmethyl)-amino]-benzothiazol-2-ylsulfanylmethyl}-benzoic acid methyl ester
  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

• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DEACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2005030704A1

  公开（公告）日：2005-04-07

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  这项发明涉及抑制组蛋白去乙酰化酶。该发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。该发明还提供了治疗细胞增殖性疾病和症状的组合物和方法。
• Inhibitors of Histone Deacetylase
  申请人：Moradei Oscar

  公开号：US20080132459A1

  公开（公告）日：2008-06-05

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  本发明涉及抑制组蛋白去乙酰化酶的方法。本发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。本发明还提供了用于治疗细胞增殖性疾病和病状的组合物和方法。
• INHIBITORS OF HISTONE DEACETYLASE
  申请人：Methylgene, Inc.

  公开号：EP1663953A1

  公开（公告）日：2006-06-07
• US7868205B2
  申请人：——

  公开号：US7868205B2

  公开（公告）日：2011-01-11
• 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.