N-(5-bromo-2-hydroxybenzyl)-2-chloroacetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(5-bromo-2-hydroxybenzyl)-2-chloroacetamide
• 英文别名: N-[(5-bromo-2-hydroxyphenyl)methyl]-2-chloroacetamide
• 化学式: C₉H₉BrClNO₂
• 分子量: 278.533
• InChiKey: XPRWUZHZDWEKOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(5-bromo-2-hydroxybenzyl)-2-chloroacetamide 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 tert-butyl (5-bromo-2-hydroxybenzyl)carbamate
  参考文献：
  名称：

  Novel adamantyl retinoid-related molecules with POLA1 inhibitory activity

  摘要：

  Atypical retinoids (AR) or retinoid-related molecules (RRMs) represent a promising class of antitumor compounds. Among AR, E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid (adarotene), has been extensively investigated. In the present work we report the results of our efforts to develop new adarotene-related atypical retinoids endowed also with POLA1 inhibitory activity. The effects of the synthesized compounds on cell growth were determined on a panel of human and hematological cancer cell lines. The most promising compounds showed antitumor activity against several tumor histotypes and increased cytotoxic activity against an adarotene-resistant cell line, compared to the parent molecule. The antitumor activity of a selected compound was evaluated on HT-29 human colon carcinoma and human mesothelioma (MM487) xenografts. Particularly significant was the in vivo activity of the compound as a single agent compared to adarotene and cisplatin, against pleural mesothelioma MM487. No reduction of mice body weight was observed, thus suggesting a higher tolerability with respect to the parent compound adarotene.

  DOI：

  10.1016/j.bioorg.2020.104253
• 作为产物：
  描述：

  4-溴苯酚 、 氯乙酰胺-N-甲醇 在 硫酸 、 溶剂黄146 作用下， 反应 96.0h， 以36%的产率得到N-(5-bromo-2-hydroxybenzyl)-2-chloroacetamide
  参考文献：
  名称：

  Novel adamantyl retinoid-related molecules with POLA1 inhibitory activity

  摘要：

  Atypical retinoids (AR) or retinoid-related molecules (RRMs) represent a promising class of antitumor compounds. Among AR, E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid (adarotene), has been extensively investigated. In the present work we report the results of our efforts to develop new adarotene-related atypical retinoids endowed also with POLA1 inhibitory activity. The effects of the synthesized compounds on cell growth were determined on a panel of human and hematological cancer cell lines. The most promising compounds showed antitumor activity against several tumor histotypes and increased cytotoxic activity against an adarotene-resistant cell line, compared to the parent molecule. The antitumor activity of a selected compound was evaluated on HT-29 human colon carcinoma and human mesothelioma (MM487) xenografts. Particularly significant was the in vivo activity of the compound as a single agent compared to adarotene and cisplatin, against pleural mesothelioma MM487. No reduction of mice body weight was observed, thus suggesting a higher tolerability with respect to the parent compound adarotene.

  DOI：

  10.1016/j.bioorg.2020.104253

文献信息

• [EN] AGENTS FOR TREATING DISORDERS INVOLVING MODULATION OF RYANODINE RECEPTORS<br/>[FR] AGENTS DE TRAITEMENT DE TROUBLES COMPRENANT LA MODULATION DE RÉCEPTEURS DE LA RYANODINE
  申请人：ARMGO PHARMA INC

  公开号：WO2008144483A2

  公开（公告）日：2008-11-27

  [EN] The present invention provides new agents and compounds effective for treating disorders and diseases associated with RyRs, including cardiac, muscular and cognitive disorders and diseases. These agents are derivatives of benzoxazepines, benzodiazepines and benzazapines. More particularly, the invention provides compounds which include derivatives of benzoxazepine, and their enantiomers, diastereomers, tautomers, pharmaceutically acceptable salts, hydrates, solvates, complexes, polymorphs, metabolites, and prodrugs thereof.
  [FR] La présente invention concerne de nouveaux agents et composés efficaces pour traiter des troubles et des maladies associés aux récepteurs de la ryanodine, comprenant les troubles et maladies cardiaques, musculaires et cognitifs. Les agents sont des dérivés de benzoxazépines, benzodiazépines et benzazapines. Plus particulièrement, l'invention concerne des composés comprenant des dérivés de benzoxazépine, et leurs énantiomères, diastéréomères, tautomères, les sels, hydrates, solvates, complexes, formes polymorphes, métabolites, et promédicaments pharmaceutiquement acceptables de ceux-ci.
• Novel adamantyl retinoid-related molecules with POLA1 inhibitory activity
  作者：Raffaella Cincinelli、Loana Musso、Mario B. Guglielmi、Ilaria La Porta、Alessandra Fucci、Egildo Luca D'Andrea、Francesco Cardile、Fabiana Colelli、Giacomo Signorino、Nadine Darwiche、Silvia Gervasoni、Giulio Vistoli、Claudio Pisano、Sabrina Dallavalle

  DOI：10.1016/j.bioorg.2020.104253

  日期：2020.11

  Atypical retinoids (AR) or retinoid-related molecules (RRMs) represent a promising class of antitumor compounds. Among AR, E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid (adarotene), has been extensively investigated. In the present work we report the results of our efforts to develop new adarotene-related atypical retinoids endowed also with POLA1 inhibitory activity. The effects of the synthesized compounds on cell growth were determined on a panel of human and hematological cancer cell lines. The most promising compounds showed antitumor activity against several tumor histotypes and increased cytotoxic activity against an adarotene-resistant cell line, compared to the parent molecule. The antitumor activity of a selected compound was evaluated on HT-29 human colon carcinoma and human mesothelioma (MM487) xenografts. Particularly significant was the in vivo activity of the compound as a single agent compared to adarotene and cisplatin, against pleural mesothelioma MM487. No reduction of mice body weight was observed, thus suggesting a higher tolerability with respect to the parent compound adarotene.