N-(m-tolyl)benzo[d]oxazol-2-amine | 39208-61-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: N-(m-tolyl)benzo[d]oxazol-2-amine
• 英文别名: N-(3-methylphenyl)-1,3-benzoxazol-2-amine
• CAS: 39208-61-2
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: YJUJZVVAAWUMAX-UHFFFAOYSA-N

物化性质

• 沸点：
  361.2±35.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-巯基苯并恶唑 在 氯化亚砜 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-(m-tolyl)benzo[d]oxazol-2-amine
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking study of N -arylbenzo[ d ]oxazol-2-amines as potential α-glucosidase inhibitors

  摘要：

  A novel series of N-arylbenzo[d]oxazol-2-amines (4a-4m) were synthesized and evaluated for their alpha-glucosidase inhibitory activity. Compounds 4f-4i, 4k and 4m displayed potent inhibitory activity against alpha-glucosidase with IC50 values in the range of 32.49 +/- 0.17-120.24 +/- 0.51 mu M as compared to the standard drug acarbose. Among all tested compounds, compound 4g having 4-phenoxy substitution at the phenyl ring was found to be the most active inhibitor of ot-glucosidase with an IC50 value of 32.49 +/- 0.17 mu M. Analysis of the kinetics of enzyme inhibition indicated that compound 4g is a noncompetitive inhibitor of alpha-glucosidase with a K-i value of 31.33 mu M. Binding interaction of compound 4g with alpha-glucosidase was explored by molecular docking simulation. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.061

文献信息

• [EN] HEPATITIS B ANTIVIRAL AGENTS<br/>[FR] AGENTS ANTIVIRAUX DE L'HÉPATITE B
  申请人：ENANTA PHARM INC

  公开号：WO2017015451A1

  公开（公告）日：2017-01-26

  The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: X-A1-Y-A2-Z-L-R (I) which inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV life cycle of the hepatitis B virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HBV infection. The invention also relates to methods of treating an HBV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明揭示了化合物的结构式（I），或其药用可接受的盐、酯或前药：X-A1-Y-A2-Z-L-R（I），这些化合物能够抑制由乙型肝炎病毒（HBV）编码的蛋白质，或干扰乙型肝炎病毒的生命周期功能，同时也可作为抗病毒药物使用。本发明还涉及包含上述化合物的药物组合物，用于治疗患有HBV感染的受试者。该发明还涉及通过给受试者投予包含本发明化合物的药物组合物来治疗HBV感染的方法。
• HEPATITIS B ANTIVIRAL AGENTS
  申请人：Enanta Pharmaceuticals, Inc.

  公开号：US20170022150A1

  公开（公告）日：2017-01-26

  The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: X-A 1 -Y-A 2 -Z-L-R  (I) which inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV life cycle of the hepatitis B virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HBV infection. The invention also relates to methods of treating an HBV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明揭示了化合物的化学式（I），或其药学上可接受的盐、酯或前药：X-A1-Y-A2-Z-L-R（I），这些化合物抑制由乙型肝炎病毒（HBV）编码的蛋白质或干扰乙型肝炎病毒的生命周期功能，并且还可用作抗病毒剂。本发明还涉及包括上述化合物的药物组合物，用于给患有HBV感染的受试者进行治疗。该发明还涉及通过给予包含本发明化合物的药物组合物来治疗受试者的HBV感染的方法。
• A Cu₂O/TBAB-promoted approach to synthesize heteroaromatic 2-amines <i>via</i> one-pot cyclization of aryl isothiocyanates with <i>ortho</i>-substituted amines in water
  作者：Jinli Zhang、Ling Chen、Yibo Dong、Jinchen Yang、Yangjie Wu

  DOI：10.1039/d0ob01431a

  日期：——

  An efficient approach to synthesize heteroaromatic 2-amines from one-pot desulfurization/dehydrogenative cyclization of aryl isothiocyanates with ortho-substituted amines in water was developed. This approach tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to synthesize heteroaromatic 2-amines in moderate to excellent yields.

  开发了一种在水中用邻位取代胺一锅法脱硫/脱氢环化芳基异硫氰酸酯合成杂芳族 2-胺的有效方法。这种方法在芳环上具有多种官能团，提供了一种实用且环境友好的方法，可以以中等至优异的产率合成杂芳族 2-胺。提出了一种似是而非的机制，并借助 ESI 质谱法提出了 TBAB 和 Cu 2 O 在本策略中的作用。
• [EN] HETEROCYCLIC COMPOUNDS AS AHR MODULATORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES EN TANT QUE MODULATEURS DE L'AHR
  申请人：JAGUAHR THERAPEUTICS PTE LTD

  公开号：WO2020043880A1

  公开（公告）日：2020-03-05

  The present invention relates compounds of the general formula (I) or (III) which are ARH inhibitors, methods for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds and pharmaceutical compositions for the treatment or prevention of diseases, in particular cancer or conditions with dysregulated immune functions, or other conditions associated with aberrant AHR signalling, as a sole agent of in combination with other active ingredients. Such compounds may also be of utility in the expansion of hematopoietic stem cells (HSCs) and the use of HSCs in autologous or allogenic transplantation for the treatment of patients with inherited immunological and autoimmune diseases and diverse hematopoietic disorders.

  本发明涉及一般式(I)或(III)的化合物，这些化合物是ARH抑制剂，制备这些化合物的方法，含有这些化合物的药物组合物和配方以及利用这些化合物和药物组合物治疗或预防疾病，特别是癌症或免疫功能失调的情况，或与异常AHR信号相关的其他病症，作为单一药剂或与其他活性成分组合使用。这些化合物还可能在扩展造血干细胞（HSCs）方面具有用途，并且利用HSCs进行自体或同种异体移植，用于治疗患有遗传免疫和自身免疫疾病以及多种造血障碍的患者。
• Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous media<i>via</i>tandem addition–cyclization
  作者：Thao Nguyen Thanh Huynh、Theeranon Tankam、Shinichi Koguchi、Tanawat Rerkrachaneekorn、Mongkol Sukwattanasinitt、Sumrit Wacharasindhu

  DOI：10.1039/d1gc01131f

  日期：——

  An electrochemical synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates was successfully developed in a one-pot fashion. Using inexpensive and widely available NaI and NaCl co-operatively in catalytic amounts, our electrosynthesis approach provided various 2-aminobenzoxazole products in moderate to high yields in an open-flask type undivided cell without using any external supporting

  以一锅法成功开发了由 2-氨基苯酚和异硫氰酸酯电化学合成 2-氨基苯并恶唑。我们的电合成方法以催化量合作使用廉价且广泛可用的 NaI 和 NaCl，在不使用任何外部支持电解质和碱的情况下，在开放式烧瓶型未分隔电池中以中等至高产率提供各种 2-氨基苯并恶唑产品。该协议可用于以中等产率从相应的 2-苯硫酚合成 2-氨基苯并噻唑。该协议有很多好处。它不含金属且具有高度可扩展性，并在温和条件下使用廉价的介质和乙醇/水作为环保溶剂。