tert-butyl 2-chloro-4-(hydroxymethyl)benzoate | 1190947-53-5

• 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: tert-butyl 2-chloro-4-(hydroxymethyl)benzoate
• CAS: 1190947-53-5
• 化学式: C₁₂H₁₅ClO₃
• 分子量: 242.702
• InChiKey: SQPWQVAKTIISLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-chloro-4-(hydroxymethyl)benzoate 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 tert-butyl 2-chloro-4-(methylsulfonylmethyl)benzoate
  参考文献：
  名称：

  Second generation 2-pyridyl biphenyl amide inhibitors of the hedgehog pathway

  摘要：

  Potent and efficacious inhibitors of the hedgehog pathway for the treatment of cancer have been prepared using the 2-pyridyl biphenyl amide scaffold common to the clinical lead GDC-0449. Analogs with polar groups in the para-position of the aryl amide ring optimized potency, had minimal CYP inhibition, and possessed good exposure in rats. Compounds 9d and 14f potently inhibited hedgehog signaling as measured by Gli1 mRNA and were found to be equivalent or more potent than GDC-0449, respectively, when studied in a Ptch(+/) medulloblastoma allograft model, that is, highly dependent on hedgehog signaling. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.134
• 作为产物：
  描述：

  2-氯对苯二甲酸二甲酯 在 sodium tetrahydroborate 、 硫酸 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 tert-butyl 2-chloro-4-(hydroxymethyl)benzoate
  参考文献：
  名称：

  Second generation 2-pyridyl biphenyl amide inhibitors of the hedgehog pathway

  摘要：

  Potent and efficacious inhibitors of the hedgehog pathway for the treatment of cancer have been prepared using the 2-pyridyl biphenyl amide scaffold common to the clinical lead GDC-0449. Analogs with polar groups in the para-position of the aryl amide ring optimized potency, had minimal CYP inhibition, and possessed good exposure in rats. Compounds 9d and 14f potently inhibited hedgehog signaling as measured by Gli1 mRNA and were found to be equivalent or more potent than GDC-0449, respectively, when studied in a Ptch(+/) medulloblastoma allograft model, that is, highly dependent on hedgehog signaling. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.134

文献信息

• Pyridyl inhibitors of hedgehog signalling
  申请人：Gunzner L. Janet

  公开号：US20060063779A1

  公开（公告）日：2006-03-23

  The invention provides novel inhibitors of hedgehog signaling that are useful as a therapeutic agents for treating malignancies where the compounds have the general formula I: wherein A, X, Y R 1 , R 2 , R 3 , R 4 , m and n are as described herein.

  这项发明提供了一种新型的刺刺信号抑制剂，可用作治疗恶性肿瘤的治疗剂，其中化合物具有一般式I： 其中A、X、Y、R1、R2、R3、R4、m和n如本文所述。
• PYRIDYL INHIBITORS OF HEDGEHOG SIGNALLING
  申请人：GUNZNER Janet L.

  公开号：US20110092461A1

  公开（公告）日：2011-04-21

  The invention provides novel inhibitors of hedgehog signaling that are useful as a therapeutic agents for treating malignancies where the compounds have the general formula I: wherein A, X, Y R 1 , R 2 , R 3 , R 4 , m and n are as described herein.

  本发明提供了新型的刺猬信号抑制剂，可用作治疗恶性肿瘤的治疗剂，其中化合物具有一般式I：其中A、X、Y、R1、R2、R3、R4、m和n如本文所述。
• [EN] PYRIDYL INHIBITORS OF HEDGEHOG SIGNALLING<br/>[FR] INHIBITEURS PYRIDYLES DE LA SIGNALISATION HEDGEHOG
  申请人：GENENTECH INC

  公开号：WO2006028958A2

  公开（公告）日：2006-03-16

  The invention provides novel inhibitors of hedgehog signaling that are useful as a therapeutic agents for treating malignancies where the compounds have the general formula I: wherein A, X, Y, R1, R2, R3, R4, and n are as described herein.

  本发明提供了新型的刺猬信号抑制剂，可用作治疗恶性肿瘤的治疗剂，其中化合物具有I式的一般公式，其中A，X，Y，R1，R2，R3，R4和n如本文所述。
• [EN] PYRIDYL INHIBITORS OF HEDGEHOG SIGNALLING<br/>[FR] INHIBITEURS PYRIDILES DE SIGNALISATION HEDGEHOG
  申请人：GENENTECH INC

  公开号：WO2009126863A3

  公开（公告）日：2009-12-23
• US7888364B2
  申请人：——

  公开号：US7888364B2

  公开（公告）日：2011-02-15