4-氯-6-(3,4-二甲氧基苯基)-2-嘧啶胺 | 645401-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 4-氯-6-(3,4-二甲氧基苯基)-2-嘧啶胺
• 英文名称: 4-Chloro-6-(3,4-dimethoxy-phenyl)-pyrimidin-2-ylamine
• 英文别名: 4-Chloro-6-(3,4-dimethoxyphenyl)pyrimidin-2-amine
• CAS: 645401-60-1
• 化学式: C₁₂H₁₂ClN₃O₂
• 分子量: 265.699
• InChiKey: HLMJWADPGOTIAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-氯-6-(3,4-二甲氧基苯基)-2-嘧啶胺 在 N,O-双三甲硅基乙酰胺 作用下， 以 正丁醇 为溶剂， 生成 7-(3,4-Dimethoxy-phenyl)-2-furan-2-yl-[1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine
  参考文献：
  名称：

  2-(2-Furanyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidin-5-amine analogs: Highly potent, orally active, adenosine A2A antagonists. Part 1

  摘要：

  The structure-activity relationship of this novel class of compounds based on 2-(2-furanyl)-7-phenyl[1,2,4]-triazolo[1,5-c]pyrimidin-5-amine, 1, and its analogs was evaluated for their in vitro and in vivo adenosine A(2A) receptor antagonism. Several compounds displayed oral activity at 3 mg/kg in a rat catalepsy model. Specifically, compound 8g displayed an excellent in vitro profile, as well as a highly promising in vivo profile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.086
• 作为产物：
  描述：

  2-氨基-4,6-二氯嘧啶 、 3,4-二甲氧基苯硼酸 在 palladium diacetate sodium carbonate 、 三苯基膦 作用下， 以 乙二醇二甲醚 为溶剂， 生成 4-氯-6-(3,4-二甲氧基苯基)-2-嘧啶胺
  参考文献：
  名称：

  Design and synthesis of 4-[(s-triazin-2-ylamino)methyl]-N-(2-aminophenyl)-benzamides and their analogues as a novel class of histone deacetylase inhibitors

  摘要：

  Inhibition of histone deacetylases (HDAC) is emerging as a new strategy in human cancer therapy. The synthesis and biological evaluation of a variety of 4-(heteroaryl aminomethyl)-N-(2-aminophenyl)-benzamides is presented herein. From the different series bearing a six-membered heteroaromatic ring studied, the s-triazine series showed the best HDAC1 enzyme and in vitro anti-proliferative activities with IC50 values below micromolar range. Some of these compounds can also significantly reduce tumor growth in human tumor xenograft models in mice. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.009

文献信息

• Methods for specifically inhibiting histone deacetylase-7 and 8
  申请人：——

  公开号：US20040072770A1

  公开（公告）日：2004-04-15

  This invention relates to the inhibition of histone deacetylase (HDAC) expression and enzymatic activity. The invention provides methods and reagents for inhibiting HDAC-7 and HDAC-8 by inhibiting expression at the nucleic acid level or inhibiting enzymatic activity at the protein level.

  本发明涉及抑制组蛋白去乙酰化酶（HDAC）表达和酶活性的方法。本发明提供了通过在核酸水平抑制表达或在蛋白质水平抑制酶活性来抑制HDAC-7和HDAC-8的方法和试剂。
• [EN] METHODS FOR SPECIFICALLY INHIBITING HISTONE DEACETYLASE-7 AND 8<br/>[FR] PROCEDE D'INHIBITION SPECIFIQUE DE L'HISTONE DEACETYLASE-7 ET 8
  申请人：METHYLGENE INC

  公开号：WO2004005513A2

  公开（公告）日：2004-01-15

  This invention relates to the inhibition of histone deacetylase (HDAC) expression and enzymatic activity. The invention provides methods and reagents for inhibiting HDAC-7 and HDAC-8 by inhibiting expression at the nucleic acid level or inhibiting enzymatic activity at the protein level.
• [DE] AMINOPYRYMIDINDERIVATE<br/>[EN] AMINO PYRYMIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE L'AMINOPYRYMIDINE
  申请人：MERCK PATENT GMBH

  公开号：WO2007098835A1

  公开（公告）日：2007-09-07

  [EN] The invention relates to novel amino pyrimidine derivatives according to claim 1. Said derivatives are HSP90 inhibitors and can be used to produce a medicament for treating diseases, in which the inhibition, regulation and/or modulation of HSP90 plays a part.
  [FR] De nouveaux dérivés d'aminopyrimidine selon la revendication 1 sont des inhibiteurs de HSP90 et peuvent être utilisés pour la production d'un médicament destiné au traitement de maladies pour lesquelles l'inhibition, la régulation et/ou la modulation de HSP90 jouent un rôle.
  [DE] Neue Aminopyrimidinderivate nach Anspruch 1 sind HSP90-lnhibitoren und können zur Herstellung eines Arzneimittels zur Behandlung von Krankheiten, bei denen die Hemmung, Regulierung und/oder Modulation von HSP90 eine Rolle spielt, verwendet werden.
• 2-(2-Furanyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidin-5-amine analogs: Highly potent, orally active, adenosine A2A antagonists. Part 1
  作者：Julius J. Matasi、John P. Caldwell、Hongtao Zhang、Ahmad Fawzi、Mary E. Cohen-Williams、Geoffrey B. Varty、Deen B. Tulshian

  DOI：10.1016/j.bmcl.2005.05.086

  日期：2005.8

  The structure-activity relationship of this novel class of compounds based on 2-(2-furanyl)-7-phenyl[1,2,4]-triazolo[1,5-c]pyrimidin-5-amine, 1, and its analogs was evaluated for their in vitro and in vivo adenosine A(2A) receptor antagonism. Several compounds displayed oral activity at 3 mg/kg in a rat catalepsy model. Specifically, compound 8g displayed an excellent in vitro profile, as well as a highly promising in vivo profile. (c) 2005 Elsevier Ltd. All rights reserved.
• Design and synthesis of 4-[(s-triazin-2-ylamino)methyl]-N-(2-aminophenyl)-benzamides and their analogues as a novel class of histone deacetylase inhibitors
  作者：Isabelle Paquin、Stéphane Raeppel、Silvana Leit、Frédéric Gaudette、Nancy Zhou、Oscar Moradei、Oscar Saavedra、Naomy Bernstein、Franck Raeppel、Giliane Bouchain、Sylvie Fréchette、Soon H. Woo、Arkadii Vaisburg、Marielle Fournel、Ann Kalita、Marie-France Robert、Aihua Lu、Marie-Claude Trachy-Bourget、Pu Theresa Yan、Jianhong Liu、Jubrail Rahil、A. Robert MacLeod、Jeffrey M. Besterman、Zuomei Li、Daniel Delorme

  DOI：10.1016/j.bmcl.2007.12.009

  日期：2008.2

  Inhibition of histone deacetylases (HDAC) is emerging as a new strategy in human cancer therapy. The synthesis and biological evaluation of a variety of 4-(heteroaryl aminomethyl)-N-(2-aminophenyl)-benzamides is presented herein. From the different series bearing a six-membered heteroaromatic ring studied, the s-triazine series showed the best HDAC1 enzyme and in vitro anti-proliferative activities with IC50 values below micromolar range. Some of these compounds can also significantly reduce tumor growth in human tumor xenograft models in mice. (C) 2007 Elsevier Ltd. All rights reserved.