5-异丙基-1,3-噻唑-4-甲醛 | 261710-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-异丙基-1,3-噻唑-4-甲醛
• 英文名称: 5-isopropyl-thiazole-4-carbaldehyde
• 英文别名: 5-Isopropylthiazole-4-carbaldehyde；5-propan-2-yl-1,3-thiazole-4-carbaldehyde
• CAS: 261710-82-1
• 化学式: C₇H₉NOS
• 分子量: 155.221
• InChiKey: ZNCIEQFZRKIVOL-UHFFFAOYSA-N

物化性质

• 沸点：
  255.3±28.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-异丙基-1,3-噻唑-4-甲醛 在 5percent Pd/BaSO₄ sodium hydroxide 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 20.0 ℃ 、220.64 kPa 条件下， 反应 47.33h， 生成 4-Hydroxy-6-isopropyl-6-[2-(5-isopropyl-thiazol-4-yl)-ethyl]-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  4-Hydroxy-5,6-dihydropyrones as Inhibitors of HIV Protease:  The Effect of Heterocyclic Substituents at C-6 on Antiviral Potency and Pharmacokinetic Parameters

  摘要：

  Due largely to the emergence of multi-drug-resistant HIV strains, the development of new HIV protease inhibitors remains a high priority for the pharmaceutical industry. Toward this end, we previously identified a 4-hydroxy-5,6-dihydropyrone lead compound (CI-1029, 1) which possesses excellent activity against the protease enzyme, good antiviral efficacy in cellular assays, and promising bioavailability in several animal species. The search for a suitable backup candidate centered on the replacement of the aniline moiety at C-6 with an appropriately substituted heterocyle. In general, this series of heterocyclic inhibitors displayed good activity (in both enzymatic and cellular tests) and-low cellular toxicity; furthermore, several analogues exhibited improved pharmacokinetic parameters in animal models. The compound with the best combination of high potency, low toxicity, and favorable bioavailabilty was (S)-3-(2-tertbutyl-4-hydroxymethy1- 5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (13-(S)). This thiophene derivative also exhibited excellent antiviral efficacy against mutant HIV protease and resistant HIV strains. For these reasons, compound 13-(S) was chosen for further preclinical evaluation.

  DOI：

  10.1021/jm0003844
• 作为产物：
  描述：

  5-异丙基噻唑-4-羧酸甲酯 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 5-异丙基-1,3-噻唑-4-甲醛
  参考文献：
  名称：

  HIV protease inhibitors

  摘要：

  本发明涉及具有改进药理特性的新型带有连环杂环的二氢吡喃，能有效抑制HIV天冬氨酸蛋白酶，阻断HIV的感染性。这些二氢吡喃在开发治疗病毒感染和疾病，包括艾滋病的疗法方面是有用的。本发明还涉及合成这些二氢吡喃的方法，以及在制备最终化合物中有用的中间体。

  公开号：

  US06528510B1

文献信息

• HIV protease inhibitors
  申请人：Warner-Lambert Company

  公开号：US06528510B1

  公开（公告）日：2003-03-04

  The present invention relates to novel dihydropyrones with tethered heterocycles having improved pharmacologic properties which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The dihydropyrones are useful in the development of therapies for the treatment of viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of the dihydropyrones and intermediates useful in the preparation of the final compounds.

  本发明涉及具有改进药理特性的新型带有连环杂环的二氢吡喃，能有效抑制HIV天冬氨酸蛋白酶，阻断HIV的感染性。这些二氢吡喃在开发治疗病毒感染和疾病，包括艾滋病的疗法方面是有用的。本发明还涉及合成这些二氢吡喃的方法，以及在制备最终化合物中有用的中间体。
• HIV PROTEASE INHIBITORS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP1112269A2

  公开（公告）日：2001-07-04
• US6528510B1
  申请人：——

  公开号：US6528510B1

  公开（公告）日：2003-03-04
• US6852711B2
  申请人：——

  公开号：US6852711B2

  公开（公告）日：2005-02-08
• [EN] HIV PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTEASE DU VIH
  申请人：WARNER LAMBERT CO

  公开号：WO2000015634A2

  公开（公告）日：2000-03-23

  The present invention relates to novel dihydropyrones with tethered heterocycles having improved pharmacologic properties which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The dihydropyrones are useful in the development of therapies for the treatment of viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of the dihydropyrones and intermediates useful in the preparation of the final compounds.