2-(3-amino-4-methylphenyl)benzoxazole | 292644-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-amino-4-methylphenyl)benzoxazole
• 英文别名: 5-(1,3-Benzoxazol-2-yl)-2-methylaniline
• CAS: 292644-38-3
• 化学式: C₁₄H₁₂N₂O
• mdl: MFCD00579038
• 分子量: 224.262
• InChiKey: KXXDLQRHCXWKCH-UHFFFAOYSA-N

物化性质

• 沸点：
  379.6±35.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(3-amino-4-methylphenyl)benzoxazole 、 2-氯-5-硝基苯甲酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以20%的产率得到N-[5-(1,3-benzoxazol-2-yl)-2-methylphenyl]-2-chloro-5-nitrobenzamide
  参考文献：
  名称：

  Optimization of Chloronitrobenzamides (CNBs) as Therapeutic Leads for Human African Trypanosomiasis (HAT)

  摘要：

  We previously reported the discovery of the activity of chloronitrobenzamides (CNBs) against bloodstream forms of Trypanosoma brucei. Herein we disclose extensive structure activity relationship and structure property relationship studies aimed at identification of tractable early leads for clinical development. These studies revealed a promising lead compound, 17b, that exhibited nanomolar potency against T. brucei (EC50 = 27 nM for T. b. brucei, 7 nM for T. b. rhodesiense, and 2 nM for T. b. gambiense) with excellent selectivity for parasite cells relative to mammalian cell lines (EC50 > 25 mu M). In addition compound 17b displayed suitable physiochemical characteristics and microsomal stability (t(1/2) > 4 h for human and mouse) to justify pursuing in vivo studies.

  DOI：

  10.1021/jm301687p
• 作为产物：
  描述：

  2-氨基苯酚 、 3-氨基-4-甲基苯甲酸 生成 2-(3-amino-4-methylphenyl)benzoxazole
  参考文献：
  名称：

  Phthalimide carboxylic acid derivatives

  摘要：

  本发明涉及公式（I）的邻苯二甲酰亚胺羧酸衍生物，其制备方法，包含它们的制药组合物以及它们在医学上的用途，特别是在癌症治疗中。其中，X为O或S；R1是公式（II）的邻苯二甲酰亚胺羧酸基团。R为氢，C1-C6烷基，芳基或C1-C3烷基芳基，而R2，R3和R4代表各种取代基。

  公开号：

  US20050203153A1

文献信息

• [EN] PHTHALIMIDE CARBOXYLIC ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDES CARBOXYLIQUES PHTALIMIDIQUES
  申请人：OXFORD GLYCOSCIENCES UK LTD

  公开号：WO2003074516A1

  公开（公告）日：2003-09-12

  The present invention relates to phthalimide carboxylic acid derivatives of formula (I), methods for their preparation, pharmaceutical compositions containing them and their use in medicine, specifically in the treatment of cancer. (I), wherein X is O or S; R1 is a phthalimide carboxylic acid group of formula (II). R is hydrogen, C1-C6 alkyl, aryl or C1-C3 alkylaryl and R2, R3 and R4 represent various substituents.

  本发明涉及公式（I）的邻苯二甲酰亚胺羧酸衍生物，其制备方法，含有它们的药物组合物以及它们在医学中的应用，具体用于癌症治疗。在公式（I）中，X为O或S；R1为公式（II）的邻苯二甲酰亚胺羧酸基团。R为氢、C1-C6烷基、芳基或C1-C3烷基芳基，R2、R3和R4代表各种取代基。
• Optimization of Orally Bioavailable Antileishmanial 2,4,5-Trisubstituted Benzamides
  作者：Ho Shin Kim、Diana Ortiz、Tara Man Kadayat、Corinne M. Fargo、Jared T. Hammill、Yizhe Chen、Amy L. Rice、Kristin L. Begley、Gaurav Shoeran、William Pistel、Phillip A. Yates、Marco A. Sanchez、Scott M. Landfear、R. Kiplin Guy

  DOI：10.1021/acs.jmedchem.3c00056

  日期：2023.6.8

  difficulty of use, and emerging drug resistance to all approved therapies. We discovered 2,4,5-trisubstituted benzamides (4) that possess potent antileishmanial activity but poor aqueous solubility. Herein, we disclose our optimization of the physicochemical and metabolic properties of 2,4,5-trisubstituted benzamide that retains potency. Extensive structure–activity and structure–property relationship

  利什曼病是一种由利什曼原虫寄生虫引起的被忽视的热带疾病，每年影响全世界超过 100 万人。由于成本高、副作用严重、疗效差、使用困难以及对所有已批准疗法出现耐药性，利什曼病的治疗选择受到限制。我们发现 2,4,5-三取代苯甲酰胺 ( 4 ) 具有有效的抗利什曼活性，但水溶性较差。在此，我们公开了对保留效力的 2,4,5-三取代苯甲酰胺的物理化学和代谢特性的优化。广泛的结构-活性和结构-性质关系研究允许选择具有适当效力、微粒体稳定性和改善进展溶解度的早期先导化合物。早期先导化合物79表现出 80% 的口服生物利用度，并能有效阻止小鼠模型中利什曼原虫的增殖。这些苯甲酰胺早期先导药物适合开发为口服抗利什曼药物。
• Optimization of the electrophile of chloronitrobenzamide leads active against Trypanosoma brucei
  作者：Jong Yeon Hwang、David C. Smithson、Gloria Holbrook、Fangyi Zhu、Michele C. Connelly、Marcel Kaiser、Reto Brun、R. Kiplin Guy

  DOI：10.1016/j.bmcl.2013.05.049

  日期：2013.7

  We previously reported the phenylchloronitrobenzamides (PCNBs), a novel class of compounds active against the species of trypanosomes that cause Human African Trypanosomiasis (HAT). Herein, we explored the potential to adjust the reactivity of the electrophilic chloronitrobenzamide core. These studies identified compound 7d that potently inhibited the growth of trypanosomes (EC50 = 120 nM for Trypanosoma b. brucei, 18 nM for Trypanosoma b. rhodesiense, and 38 nM for Trypanosoma b. gambiense) without significant cytotoxicity against mammalian cell lines (EC50 > 25 mu M for HepG2, HEK293, Raji, and BJ cell lines) and also had good stability in microsomal models (t(1/2) > 4 h in both human and mouse). Overall these properties indicate the compound 7d and its analogs are worth further exploration as potential leads for HAT. (C) 2013 Elsevier Ltd. All rights reserved.
• PHTHALIMIDE CARBOXYLIC ACID DERIVATIVES
  申请人：Oxford GlycoSciences (UK) Ltd,Attn: Mary Gadsden

  公开号：EP1483261A1

  公开（公告）日：2004-12-08
• US7138425B2
  申请人：——

  公开号：US7138425B2

  公开（公告）日：2006-11-21