5-(4-(4-methoxyphenylamino)quinazolin-2-yl)benzene-1,2,3-triol | 1251839-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-(4-(4-methoxyphenylamino)quinazolin-2-yl)benzene-1,2,3-triol
• 英文别名: 5-[4-(4-Methoxyanilino)quinazolin-2-yl]benzene-1,2,3-triol；5-[4-(4-methoxyanilino)quinazolin-2-yl]benzene-1,2,3-triol
• CAS: 1251839-87-8
• 化学式: C₂₁H₁₇N₃O₄
• 分子量: 375.384
• InChiKey: HMYFIZXMDGCPCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)quinazolin-4-amine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 5-(4-(4-methoxyphenylamino)quinazolin-2-yl)benzene-1,2,3-triol
  参考文献：
  名称：

  Design, synthesis, and evaluation of quinazoline T cell proliferation inhibitors

  摘要：

  We report here on a class of quinazoline molecules that inhibit T cell proliferation. The most potent compound N-p-tolyl-2-(3,4,5-trimethoxyphenyl) quinazolin-4-amine (S101) and its close analogs were found to inhibit the proliferation of T cells from human peripheral blood mononuclear cells (PBMC) and Jurkat cells, with IC50 in the sub-micromolar range. The inhibitor induced G2 cell cycle arrest but did not inhibit IL-2 secretion. The anti-proliferative effect correlated with inhibition of the tyrosine phosphorylation of SLP-76, a molecular element in the signaling pathway of the T cell receptor (TCR). The inhibitor restrained proliferation of lymphocytes with much higher potency than non-hematopoietic cells. This new class of specific T cell proliferation inhibitors may serve as lead molecules for the development of agents aimed at diseases in which T cell signaling plays a role and agents to induce tolerance to grafted tissues or organs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.004

文献信息

• [EN] QUINAZOLINE-BASED T CELL PROLIFERATION INHIBITORS<br/>[FR] INHIBITEURS DE LA PROLIFÉRATION DES LYMPHOCYTES T À BASE DE QUINAZOLINE
  申请人：YISSUM RES DEV CO

  公开号：WO2011092695A1

  公开（公告）日：2011-08-04

  Quinazoline derivatives are provided that specifically inhibit proliferation of T cells without affecting the level of IL-2 secreted from said T cells. These compounds as well as pharmaceutical composition comprising them are useful for the treatment of indications mediated by T cell proliferation.

  提供了喹唑啉衍生物，它们特异性地抑制T细胞的增殖，而不影响来自该T细胞的IL-2分泌水平。这些化合物以及包含它们的药物组成物对于治疗由T细胞增殖介导的适应症是有用的。
• QUINAZOLINE-BASED T CELL PROLIFERATION INHIBITORS
  申请人：Levitzki Alexander

  公开号：US20130109706A1

  公开（公告）日：2013-05-02

  Quinazoline derivatives are provided that specifically inhibit proliferation of T cells without affecting the level of IL-2 secreted from said T cells. These compounds as well as pharmaceutical composition comprising them are useful for the treatment of indications mediated by T cell proliferation.

  提供了喹唑啉衍生物，可特异性抑制T细胞增殖，而不影响该T细胞分泌的IL-2水平。这些化合物以及包含它们的药物组合物对于治疗由T细胞增殖介导的症状是有用的。
• US8759363B2
  申请人：——

  公开号：US8759363B2

  公开（公告）日：2014-06-24
• Design, synthesis, and evaluation of quinazoline T cell proliferation inhibitors
  作者：Idit Sagiv-Barfi、Ester Weiss、Alexander Levitzki

  DOI：10.1016/j.bmc.2010.07.004

  日期：2010.9

  We report here on a class of quinazoline molecules that inhibit T cell proliferation. The most potent compound N-p-tolyl-2-(3,4,5-trimethoxyphenyl) quinazolin-4-amine (S101) and its close analogs were found to inhibit the proliferation of T cells from human peripheral blood mononuclear cells (PBMC) and Jurkat cells, with IC50 in the sub-micromolar range. The inhibitor induced G2 cell cycle arrest but did not inhibit IL-2 secretion. The anti-proliferative effect correlated with inhibition of the tyrosine phosphorylation of SLP-76, a molecular element in the signaling pathway of the T cell receptor (TCR). The inhibitor restrained proliferation of lymphocytes with much higher potency than non-hematopoietic cells. This new class of specific T cell proliferation inhibitors may serve as lead molecules for the development of agents aimed at diseases in which T cell signaling plays a role and agents to induce tolerance to grafted tissues or organs. (C) 2010 Elsevier Ltd. All rights reserved.