5-甲基-N-苯基-1,2-恶唑-3-甲酰胺 | 99984-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-甲基-N-苯基-1,2-恶唑-3-甲酰胺
• 英文名称: 5-methyl-3-(N-phenylcarbamoyl)isoxazole
• 英文别名: 5-methyl-isoxazole-3-carboxylic acid anilide；5-Methyl-isoxazol-3-carbonsaeure-anilid；3-Isoxazolecarboxamide, 5-methyl-N-phenyl-；5-methyl-N-phenyl-1,2-oxazole-3-carboxamide
• CAS: 99984-65-3
• 化学式: C₁₁H₁₀N₂O₂
• mdl: MFCD00667039
• 分子量: 202.213
• InChiKey: GTLOCKIDPCWRKU-UHFFFAOYSA-N

物化性质

• 熔点：
  133-135 °C(Solv: benzene (71-43-2))
• 沸点：
  284.7±28.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-甲基-N-苯基-1,2-恶唑-3-甲酰胺 在 五氯化磷 作用下， 生成 5-methyl-N-phenyl-isoxazole-3-carboximidoyl chloride
  参考文献：
  名称：

  Quilico; Panizzi, Gazzetta Chimica Italiana, 1938, vol. 68, p. 625,635

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲基异恶唑-3-甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-甲基-N-苯基-1,2-恶唑-3-甲酰胺
  参考文献：
  名称：

  异恶唑向吡唑的直接转化：更新和改进

  摘要：

  通过在环境温度下在氢化催化剂例如阮内镍的存在下用肼在甲醇中处理，将具有烷基或氨基甲酰基的异恶唑高产率地转化成相应的吡唑。为了合成N-取代的吡唑，需要将异恶唑氢解，然后用取代的肼处理。3（5）-芳基或酰基酰胺基取代的异恶唑不太适合这种转化。

  DOI：

  10.1016/j.tet.2007.09.046

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。
• Isoxazole derivatives and methods of treating nitric oxide mediated diseases
  申请人：Shaw Jiajiu

  公开号：US20060223873A1

  公开（公告）日：2006-10-05

  A series of isoxazole derivatives and methods of suppressing, inhibiting, or preventing disorders mediated by nitric oxide (NO) and/or proinflammatory cytokines, such as TNF-α (tumor necrosis factor alpha), IL-1 (interlukin-1), and IL-6, are described.

  本文描述了一系列异唑啉衍生物及其抑制、抑制或预防由一氧化氮(NO)和/或促炎细胞因子引起的疾病的方法，例如TNF-α（肿瘤坏死因子α）、IL-1（白细胞介素1）和IL-6。
• Deoxygenative Radical Boration of Inert Amides via a Combination of Relay and Cooperative Catalysis
  作者：Feng Jiang、Jing'an Li、Xiaoming Wang

  DOI：10.1002/chem.202301199

  日期：2023.6.22

  One of the most challenging tasks in organic synthesis is to develop novel methodologies for rapid construction of complex molecules starting from easily available yet inert raw materials. In this context, multi‐catalysis strategies have attracted great attention in the discovery of new reactivity profiles that may allow access to many difficult or unattainable transformations. So far the deoxygenative functionalization of ubiquitous amides is usually achieved by nucleophilic attack on the imine or iminium ion intermediate formed via activation of the C=O bond, and these functionalization reagents were often confined to C‐based nucleophiles, which largely limited the diversity of the resultant amines. Herein, we disclose a combined strategy of relay and cooperative catalysis with a triple iridium‐photoredox‐organocatalysis system to achieve an unprecedented reductive boration of amides, affording valuable α‐amino boron products which are viable building blocks. In this transformation, the Ir‐catalyzed semi‐reduction of amides is successfully incorporated with photo‐organic catalyzed nucleophilic boryl radical addition, thus delivering the corresponding α‐boryl amines in high efficiency.

  摘要 有机合成领域最具挑战性的任务之一是开发新型方法，以便从易于获得的惰性原料出发，快速构建复杂分子。在这种情况下，多催化策略在发现新的反应性概况方面引起了极大的关注，这些反应性概况可能允许进行许多困难或无法实现的转化。迄今为止，无处不在的酰胺的脱氧官能化通常是通过亲核攻击 C=O 键活化形成的亚胺或亚铵离子中间体来实现的，而这些官能化试剂通常仅限于 C 型亲核物，这在很大程度上限制了所生成胺的多样性。在此，我们揭示了一种接力催化和协同催化的组合策略，利用三重铱-光氧化-有机催化系统实现了前所未有的酰胺还原丁化，得到了有价值的α-氨基硼产物，这些产物是可行的构筑基块。在这一转化过程中，铱催化的酰胺半还原与光催化的亲核硼酸基加成成功地结合在一起，从而高效地得到了相应的α-硼酸胺。
• New N-aryl isoxazolecarboxamides and N-isoxazolylbenzamides as anticonvulsant agents
  作者：F Lepage、F Tombret、G Cuvier、A Marivain、JM Gillardin

  DOI：10.1016/0223-5234(92)90137-p

  日期：1992.9

  We prepared a series of N-aryl isoxazolecarboxamide, N-isoxazolylbenzamide compounds and derivatives and studied their anticonvulsant action in MES and MMS tests. Some of these reveal considerable activity, especially with respect to MES test. The disubstitution in the 2.6-position on the phenyl ring by two methyl groups would appear to be of primary importance for the activity. The amide bridge between the phenyl and isoxazolic rings, whether of the anilide or benzamide type, seems to show similar anticonvulsant behavior. We have selected the derivatives 8 (N-(2.6-dimethylphenyl)-5-methyl-3-isoxazolecarboxamide, 12 (N-(2,6-dimethylphenyl)-5-hydroxymethyl-3-isoxazolecarboxamide) and 51 (N-(5-methyl-3-isoxazolyl)-2.6-dimethylbenzamide) which are presently being studied in more extended pharmacological tests.