5-(2-methoxycarbonyl-ethenyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester | 1034573-47-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-(2-methoxycarbonyl-ethenyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester
• 英文别名: 5-(2-methoxycarbonyl-vinyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester；tert-butyl 5-(3-methoxy-3-oxoprop-1-enyl)-1,3-dihydroisoindole-2-carboxylate
• CAS: 1034573-47-1
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: PRKUNGDQVHXZPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-methoxycarbonyl-ethenyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester 在 羟胺 、 sodium methylate 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 3-(2-butylsulfonyl-1,3-dihydroisoindol-5-yl)-N-hydroxyprop-2-enamide
  参考文献：
  名称：

  The design, synthesis and structure–activity relationships of novel isoindoline-based histone deacetylase inhibitors

  摘要：

  The design, synthesis and biological evaluation of a novel series of isoindoline-based hydroxamates is described. Several analogs were shown to inhibit HDAC1 with IC50 values in the low nanomolar range and inhibit cellular proliferation of HCT116 human colon cancer cells in the sub-micromolar range. The cellular potency of compound 17e was found to have greater in vitro anti-proliferative activity than several compounds in late stage clinical trials for the treatment of cancer. The in vitro safety profiles of selected compounds were assessed and shown to be suitable for further lead optimization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.015
• 作为产物：
  描述：

  4-溴邻苯二甲酰亚胺 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(2-methoxycarbonyl-ethenyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  The design, synthesis and structure–activity relationships of novel isoindoline-based histone deacetylase inhibitors

  摘要：

  The design, synthesis and biological evaluation of a novel series of isoindoline-based hydroxamates is described. Several analogs were shown to inhibit HDAC1 with IC50 values in the low nanomolar range and inhibit cellular proliferation of HCT116 human colon cancer cells in the sub-micromolar range. The cellular potency of compound 17e was found to have greater in vitro anti-proliferative activity than several compounds in late stage clinical trials for the treatment of cancer. The in vitro safety profiles of selected compounds were assessed and shown to be suitable for further lead optimization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.015

文献信息

• Heterocycle Compounds and Methods of Use Thereof
  申请人：Cho Young Shin

  公开号：US20100022514A1

  公开（公告）日：2010-01-28

  The invention relates to the use of compounds in the treatment of deacetylase-associated diseases and for the manufacture of pharmaceutical preparations for the treatment of said diseases.

  本发明涉及使用化合物治疗脱乙酰酶相关疾病，并用于制造治疗该类疾病的药物制剂。