tetrahydrothiophene-3-carbaldehyde | 1065183-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: tetrahydrothiophene-3-carbaldehyde
• 英文别名: tetrahydrothiophene-3-carboxaldehyde；tetrahydro-3-thiophenecarbaldehyde；Thiolane-3-carbaldehyde
• CAS: 1065183-51-8
• 化学式: C₅H₈OS
• 分子量: 116.184
• InChiKey: XZIKOTWVTCVFDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetrahydrothiophene-3-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以77%的产率得到3-hydroxymethyltetrahydrothiophene
  参考文献：
  名称：

  光化学同构法制备流动性脂肪醛

  摘要：

  廉价和易于获得的甲醛水溶液在与不稳定的重氮化合物的同系化反应中用作甲酰化试剂，这是通过在流动光反应器中对台式稳定的恶二唑啉进行紫外线光解而实现的。合成了各种脂族醛以及相应的衍生醇和苯并咪唑。不需要过渡金属催化剂或添加剂来影响反应，该反应在室温下进行80分钟。

  DOI：

  10.1021/acs.joc.8b02721
• 作为产物：
  描述：

  2,5-二氢噻吩-3-甲醛 在 10% palladium on charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以83.5%的产率得到tetrahydrothiophene-3-carbaldehyde
  参考文献：
  名称：

  WO2008/118724

  摘要：

  公开号：

文献信息

• Penicillins containing an acrylamide side chain
  申请人：Beecham Group p.l.c.

  公开号：US05126335A1

  公开（公告）日：1992-06-30

  Compounds of formula (I) and pharmaceutically acceptable salts and in-vivo hydrolysable esters thereof: ##STR1## wherein X is hydrogen or a group NHR.sup.1, wherein R.sup.1 is hydrogen or an amino protecting group, and R is an optionally substituted 5-membered or 6-membered saturated heterocyclic group containing 1 or 2 heteroatoms selected from oxygen, sulphur or nitrogen, are useful in the treatment of bacterial infections in humans and animals.

  公式（I）的化合物及其药用可接受盐和体内可水解酯：其中X为氢或基团NHR.sup.1，其中R.sup.1为氢或氨基保护基，R为含有1或2个来自氧、硫或氮的杂原子的可选取代的5-或6-成员饱和杂环基团，在人类和动物的细菌感染治疗中有用。
• Tetrahydroindazoles as Interleukin-2 Inducible T-Cell Kinase Inhibitors. Part II. Second-Generation Analogues with Enhanced Potency, Selectivity, and Pharmacodynamic Modulation in Vivo
  作者：Jason D. Burch、Kathy Barrett、Yuan Chen、Jason DeVoss、Charles Eigenbrot、Richard Goldsmith、M. Hicham A. Ismaili、Kevin Lau、Zhonghua Lin、Daniel F. Ortwine、Ali A. Zarrin、Paul A. McEwan、John J. Barker、Claire Ellebrandt、Daniel Kordt、Daniel B. Stein、Xiaolu Wang、Yong Chen、Baihua Hu、Xiaofeng Xu、Po-Wai Yuen、Yamin Zhang、Zhonghua Pei

  DOI：10.1021/jm501998m

  日期：2015.5.14

  The Medicinal chemistry community has directed considerable efforts toward the discovery Of selective inhibitors of interleukin-2 inducible T-cell kinase (ITK) given its role in T-cell signaling downstream of the T-cell receptor (TCR) and the implications of this target for inflammatory disorders such as asthma. We have previously disclosed a structure-and property-guided lead optimization effort which resulted in the discovery of a new series of tetrahydroindazole-containing selective ITK inhibitors. Herein we disclose further optimization of this series that resulted in further potency improvements, reduced off-target receptor binding liabilities, and reduced cytotoxicity. Specifically, we have identified a correlation between the basicity of solubilizing elements in the ITK inhibitors and off-target antiprolifetative effects, Which was exploited to reduce cytotoxicity while maintaining kinase selectivity. Optimized analogues were shown to reduce IL-2 and IL-13 production in vivo following oral or intraperitoneal dosing in mice.