methyl 2-[4-(N-boc-aminomethyl)-phenyl]-oxazole-4-carboxylate | 622847-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-[4-(N-boc-aminomethyl)-phenyl]-oxazole-4-carboxylate
• 英文别名: methyl 2-[4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]-1,3-oxazole-4-carboxylate
• CAS: 622847-16-9
• 化学式: C₁₇H₂₀N₂O₅
• 分子量: 332.356
• InChiKey: LMZAXFKNFPUPKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[4-(N-boc-aminomethyl)-phenyl]-oxazole-4-carboxylate 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[4-(Phenylacetylamino-methyl)-phenyl]-oxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Discovery and structure–activity relationship of 2-phenyl-oxazole-4-carboxamide derivatives as potent apoptosis inducers

  摘要：

  As a continuation of our efforts to discover novel apoptosis inducers as anticancer agents using a cell-based caspase HTS assay, 2-phenyl-oxazole-4-carboxamide derivatives were identified. The structure-activity relationships of this class of molecules were explored. Compound 1k, with EC50 of 270 nM and GI(50) of 229 nM in human colorectal DLD-1 cells, was selected and demonstrated the ability to cleave PARP and displayed DNA laddering, the hallmarks of apoptosis. Compound 1k showed 63% tumor growth inhibition in human colorectal DLD-1 xenograft mouse model at 50 mpk, bid. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.018
• 作为产物：
  描述：

  4-[(叔丁氧羰基氨基)甲基]苯甲酸 在 伯吉斯试剂 、 三氯溴甲烷 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl 2-[4-(N-boc-aminomethyl)-phenyl]-oxazole-4-carboxylate
  参考文献：
  名称：

  Discovery and structure–activity relationship of 2-phenyl-oxazole-4-carboxamide derivatives as potent apoptosis inducers

  摘要：

  As a continuation of our efforts to discover novel apoptosis inducers as anticancer agents using a cell-based caspase HTS assay, 2-phenyl-oxazole-4-carboxamide derivatives were identified. The structure-activity relationships of this class of molecules were explored. Compound 1k, with EC50 of 270 nM and GI(50) of 229 nM in human colorectal DLD-1 cells, was selected and demonstrated the ability to cleave PARP and displayed DNA laddering, the hallmarks of apoptosis. Compound 1k showed 63% tumor growth inhibition in human colorectal DLD-1 xenograft mouse model at 50 mpk, bid. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.018

文献信息

• [EN] ACETYLENE DERIVATIVES AS INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] DERIVES D'ACETYLENE EN TANT QU'INHIBITEURS D'HISTONE DEACETYLASE
  申请人：AXYS PHARM INC

  公开号：WO2005019174A1

  公开（公告）日：2005-03-03

  The present invention is directed to certain hydroxamate derivatives that are inhibitors of histone deacetylase and are therefore useful in the treatment of diseases associated with histone deacetylase activity. Pharmaceutical compositions and processes for preparing these compounds are also disclosed.

  本发明涉及某些羟肟酸酯衍生物，它们是组蛋白去乙酰化酶的抑制剂，因此在治疗与组蛋白去乙酰化酶活性相关的疾病方面具有用处。还公开了制备这些化合物的药物组合物和方法。
• Acetylene derivatives as inhibitors of histone deacetylase
  申请人：Sendzik Martin

  公开号：US20050131018A1

  公开（公告）日：2005-06-16

  The present invention is directed to certain hydroxamate derivatives that are inhibitors of histone deacetylase and are therefore useful in the treatment of diseases associated with histone deacetylase activity. Pharmaceutical compositions and processes for preparing these compounds are also disclosed.

  本发明涉及某些羟酸酰胺衍生物，它们是组蛋白去乙酰化酶的抑制剂，因此在治疗与组蛋白去乙酰化酶活性相关的疾病方面非常有用。还公开了制备这些化合物的制药组合物和过程。
• Novel phenyl derivatives as inducers of apoptosis
  申请人：Cai Xiong Sui

  公开号：US20050026929A1

  公开（公告）日：2005-02-03

  The present invention related to certain phenyl derivatives that are activators of caspases and inducers of apoptosis, pharmaceutical composition comprising these compounds and method of treating cancer utilizing these compounds.

  本发明涉及某些苯基衍生物，它们是caspases的激活剂和凋亡诱导剂，包括这些化合物的制药组合物以及利用这些化合物治疗癌症的方法。
• Corticotropin releasing factor antagonists
  申请人：Chen L. Yuhpyng

  公开号：US20050032846A1

  公开（公告）日：2005-02-10

  A pharmaceutical composition for treatment of a disorder or condition the treatment of which can be effected or facilitated by antagonizing Corticotropin Releasing Factor (CRF). The pharmaceutical composition includes a pharmaceutically acceptable carrier and an effective amount to treat the disorder or condition of the following compound: or a pharmaceutically acceptable salt thereof, wherein A, B, Z, R 3 , R 4 , and R 5 are as defined herein.

  一种用于治疗可以通过拮抗促肾上腺皮质激素释放因子（CRF）来治疗或促进治疗的疾病或病状的药物组合物。该药物组合物包括一种药用载体和以下化合物的有效治疗剂量或其药用可接受盐：或其药用可接受盐，其中A、B、Z、R3、R4和R5如本文所定义。
• ACETYLENE DERIVATIVES AS INHIBITORS OF HISTONE DEACETYLASE
  申请人：SENDZIK Martin

  公开号：US20080139547A1

  公开（公告）日：2008-06-12

  The present invention is directed to certain hydroxamate derivatives that are inhibitors of histone deacetylase and are therefore useful in the treatment of diseases associated with histone deacetylase activity. Pharmaceutical compositions and processes for preparing these compounds are also disclosed.

  本发明涉及某些羟肟酸衍生物，它们是组蛋白去乙酰化酶的抑制剂，因此对于治疗与组蛋白去乙酰化酶活性相关的疾病有用。同时还公开了制备这些化合物的制药组合物和过程。