ST5690 | 1232885-82-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ST5690
• 英文别名: (E)-3-(3'-adamantan-1-yl-4'-[(S)-1-(carboxymethylcarbamoyl)-3-methyl-butylcarbamoyloxy]biphenyl-4-yl)acrylic acid；(E)-3-[4-[3-(1-adamantyl)-4-[[(2S)-1-(carboxymethylamino)-4-methyl-1-oxopentan-2-yl]carbamoyloxy]phenyl]phenyl]prop-2-enoic acid
• CAS: 1232885-82-3
• 化学式: C₃₄H₄₀N₂O₇
• 分子量: 588.701
• InChiKey: OEBSZHHERNTZJZ-VSMJNIQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid tert-butyl ester 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 ST5690
  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

• New retinoid derivatives as back-ups of Adarotene
  作者：Giuseppe Giannini、Tiziana Brunetti、Gianfranco Battistuzzi、Domenico Alloatti、Gianandrea Quattrociocchi、Maria Grazia Cima、Lucio Merlini、Sabrina Dallavalle、Raffaella Cincinelli、Raffaella Nannei、Loredana Vesci、Federica Bucci、Rosanna Foderà、Mario Berardino Guglielmi、Claudio Pisano、Walter Cabri

  DOI：10.1016/j.bmc.2012.01.042

  日期：2012.4

  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.