异恶唑-3-甲腈 | 68776-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 异恶唑-3-甲腈
• 中文别名: 3-异噁唑甲腈
• 英文名称: 1,2-oxazole-3-carbonitrile
• 英文别名: isoxazole-3-carbonitrile；3-cyanoisoxazole
• CAS: 68776-57-8
• 化学式: C₄H₂N₂O
• mdl: MFCD09833404
• 分子量: 94.0727
• InChiKey: QUBXULZTCLXFRV-UHFFFAOYSA-N

物化性质

• 沸点：
  70 °C(Press: 25 Torr)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  -20°C，密封保存，并确保环境干燥。

反应信息

• 作为反应物：
  描述：

  异恶唑-3-甲腈 、 (3S,4S,5R)-2-(aminomethyl)-5-(hydroxymethyl)tetrahydrofuran-2,3,4-triol 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 43.0h， 生成 (1R,2S,3R)-1-(2-(异噁唑-3-基)-1H-咪唑-4-基)丁烷-1,2,3,4-四醇
  参考文献：
  名称：

  Inhibition of Sphingosine 1-Phosphate Lyase for the Treatment of Rheumatoid Arthritis: Discovery of (E)-1-(4-((1R,2S,3R)-1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl)ethanone Oxime (LX2931) and (1R,2S,3R)-1-(2-(Isoxazol-3-yl)-1H-imidazol-4-yl)butane-1,2,3,4-tetraol (LX2932)

  摘要：

  Sphingosine 1-phosphate lyase (S1PL) has been characterized as a novel target for the treatment of autoimmune disorders using genetic and pharmacological methods. Medicinal chemistry efforts targeting S1PL by direct in vivo evaluation of synthetic analogues of 2-acetyl-4(5)-(1(R),2(S),3(R),4-tetrahydroxy-butyl)-imidazole (THI, 1) led to the discovery of 2 (LX2931) and 4 (LX2932). The immunological phenotypes observed in S1PL deficient mice were recapitulated by oral administration of 2 or 4. Oral dosing of 2 or 4 yielded a dose-dependent decrease in circulating lymphocyte numbers in multiple species and showed a therapeutic effect in rodent models of rheumatoid arthritis (RA). Phase I clinical trials indicated that 2, the first clinically studied inhibitor of S1PL, produced a dose-dependent and reversible reduction of circulating lymphocytes and was well tolerated at dose levels of up to 180 mg daily. Phase II evaluation of 2 in patients with active rheumatoid arthritis is currently underway.

  DOI：

  10.1021/jm101183p
• 作为产物：
  描述：

  异噁唑-3-羧酰胺 在 phosphorus pentoxide 作用下， 反应 0.5h， 生成 异恶唑-3-甲腈
  参考文献：
  名称：

  与异恶唑合成；异恶唑并[2,3- a ]吡啶鎓盐的生产以及异恶唑-3-羧酸盐向恶唑-2-羧酸盐的光化学转化

  摘要：

  3-（4-乙氧基丁酰基）异恶唑（6）的环化得到4,5,6,7-四氢-4-氧代异恶唑并[2,3- a ]溴化吡啶鎓（7）。尝试用沸腾的乙酸酐对酮（7）进行芳构化未成功，但是溴化反应生成了二溴代酮（9），将其脱氢溴化为5-溴代-4-羟基异恶唑并[2,3- a ]溴化吡啶鎓（10）。 。描述了异恶唑-3-羧酸盐到相应的恶唑-2-羧酸盐的光化学转化。

  DOI：

  10.1039/j39710001196

文献信息

• METHODS OF PREPARING IMIDAZOLE-BASED BICYCLIC COMPOUNDS
  申请人：Guohua Jason

  公开号：US20090318705A1

  公开（公告）日：2009-12-24

  Methods of preparing compounds of formula I are disclosed:

  公开了制备式I化合物的方法：
• SOLID FORMS OF (1R,2S,3R)-1-(2-(ISOXAZOL-3-YL)-1H-IMIDAZOL-4-YL)BUTANE-1,2,3,4-TETRAOL AND METHODS OF THEIR USE
  申请人：Burgoon Hugh Alfred

  公开号：US20090318516A1

  公开（公告）日：2009-12-24

  Solid forms of (1R,2S,3R)-1-(2-(isoxazol-3-yl)-1H-imidazol-4-yl)butane-1,2,3,4-tetraol and hydrates thereof are disclosed, as well as compositions comprising them and methods of their use.

  固体形式的(1R,2S,3R)-1-(2-(异噁唑-3-基)-1H-咪唑-4-基)丁烷-1,2,3,4-四醇及其水合物被披露，以及包含它们的组合物和使用方法。
• [EN] NOVEL, HIGHLY ACTIVE PYRAZOLO-PIPERIDINE SUBSTITUTED INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)<br/>[FR] NOUVEAUX INDOLE-2-CARBOXAMIDES À SUBSTITUTION PYRAZOLO-PIPÉRIDINE HAUTEMENT ACTIFS AGISSANT CONTRE LE VIRUS DE L'HÉPATITE B (VHB)
  申请人：AICURIS GMBH & CO KG

  公开号：WO2019086142A1

  公开（公告）日：2019-05-09

  The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.

  本发明一般涉及新型抗病毒药剂。具体地，本发明涉及能够抑制乙型肝炎病毒（HBV）编码的蛋白质或干扰HBV复制周期功能的化合物，包含这种化合物的组合物，抑制HBV病毒复制的方法，治疗或预防HBV感染的方法，以及制备这些化合物的工艺和中间体。
• [EN] NOVEL INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)<br/>[FR] NOUVEAUX INDOLE-2-CARBOXAMIDES ACTIFS CONTRE LE VIRUS DE L'HÉPATITE B (VHB)
  申请人：AICURIS GMBH & CO KG

  公开号：WO2020221826A1

  公开（公告）日：2020-11-05

  The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.

  本发明一般涉及新型抗病毒药剂。具体地，本发明涉及能够抑制乙型肝炎病毒（HBV）编码的蛋白质或干扰HBV复制周期功能的化合物，包括这种化合物的组合物，抑制HBV病毒复制的方法，治疗或预防HBV感染的方法，以及制备这些化合物的工艺和中间体。
• [EN] COMPOUNDS AND USE THEREOF FOR THE TREATMENT OF INFECTIOUS DISEASES AND CANCER<br/>[FR] COMPOSÉS ET LEUR UTILISATION POUR LE TRAITEMENT DE MALADIES INFECTIEUSES ET DU CANCER
  申请人：AC BIOSCIENCE SA

  公开号：WO2021032857A1

  公开（公告）日：2021-02-25

  The invention provides the imidazole, oxazole and thiazole compounds and use thereof in methods for treating a disease or a disorder, such as infectious diseases and cancer, wherein inhibition of sphingosine-1-phosphate lyase is beneficial to treat the disease or the disorder.

  该发明提供了咪唑、噁唑和噻唑化合物及其在治疗疾病或障碍的方法中的应用，例如感染性疾病和癌症，其中抑制神经鞘氨醇-1-磷酸裂解酶对治疗疾病或障碍是有益的。