(E)-3-(adamantan-1-yl)-4'-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-[1,1'-biphenyl]-4-yl 4-morpholinobutanoate | 1232886-30-4

• 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: (E)-3-(adamantan-1-yl)-4'-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-[1,1'-biphenyl]-4-yl 4-morpholinobutanoate
• CAS: 1232886-30-4
• 化学式: C₃₇H₄₇NO₅
• 分子量: 585.784
• InChiKey: RRGDVUAFBXTNKJ-MDWZMJQESA-N

物化性质

• 沸点：
  712.9±60.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(adamantan-1-yl)-4'-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-[1,1'-biphenyl]-4-yl 4-morpholinobutanoate 在 盐酸 、 水 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 阿达罗汀
  参考文献：
  名称：

  New retinoid derivatives as back-ups of Adarotene

  摘要：

  Adarotene belongs to the so-called class of atypical retinoids. The presence of the phenolic hydroxyl group on Adarotene structure allows a rapid O-glucuronidation as a major mechanism of elimination of the drug, favoring a fast excretion of its glucuronide metabolite in the urines. A series of ether, carbamate and ester derivatives was synthesized. All of them were studied and evaluated for their stability at different pH. The cytotoxic activity in vitro on NCI-H460 non-small cell lung carcinoma and A2780 ovarian tumor cell lines was also tested. A potential back-up of Adarotene has been selected to be evaluated in tumor models. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.042
• 作为产物：
  描述：

  (E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid tert-butyl ester 在 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 13.0h， 生成 (E)-3-(adamantan-1-yl)-4'-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-[1,1'-biphenyl]-4-yl 4-morpholinobutanoate
  参考文献：
  名称：

  New retinoid derivatives as back-ups of Adarotene

  摘要：

  Adarotene belongs to the so-called class of atypical retinoids. The presence of the phenolic hydroxyl group on Adarotene structure allows a rapid O-glucuronidation as a major mechanism of elimination of the drug, favoring a fast excretion of its glucuronide metabolite in the urines. A series of ether, carbamate and ester derivatives was synthesized. All of them were studied and evaluated for their stability at different pH. The cytotoxic activity in vitro on NCI-H460 non-small cell lung carcinoma and A2780 ovarian tumor cell lines was also tested. A potential back-up of Adarotene has been selected to be evaluated in tumor models. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.042

文献信息

• [EN] NEW RETINOID DERIVATIVES ENDOWED WITH CYTOTOXIC AND/OR ANTIANGIOGENIC PROPERTIES<br/>[FR] NOUVEAUX DÉRIVÉS DE RÉTINOÏDES PRÉSENTANT DES PROPRIÉTÉS CYTOTOXIQUES ET/OU ANTI-ANGIOGÈNES
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2010072727A1

  公开（公告）日：2010-07-01

  The present invention relates to new retinoid derivatives of Formula (I), and to pharmaceutical compositions containing them for the treatment of patients affected by pathologies such as arthritic conditions, tumours, metastatic cancer, diabetic retinopathy, psoriasis, chronic inflammatory diseases or atherosclerosis.

  本发明涉及公式(I)的新视黄醇衍生物，以及含有它们的药物组合物，用于治疗患有关节炎、肿瘤、转移性癌症、糖尿病性视网膜病变、银屑病、慢性炎症性疾病或动脉粥样硬化等病症的患者。