trans-4-amino-tetrahydrothiophen-3-ol 1,1-dioxide | 20688-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: trans-4-amino-tetrahydrothiophen-3-ol 1,1-dioxide
• 英文别名: 3-hydroxy-4-aminothiolane 1,1-dioxide；trans-4-Aminothiolan-3-ol 1,1-dioxide；3-hydroxy-4-aminothiolan-1,1-dioxide；(+/-)-trans-4-amino-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-ol；(3R,4R)-4-amino-1,1-dioxothiolan-3-ol
• CAS: 20688-37-3；55261-00-2
• 化学式: C₄H₉NO₃S
• 分子量: 151.186
• InChiKey: REXPOWCRPFUCHS-IMJSIDKUSA-N

物化性质

• 沸点：
  424.1±45.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  硫氰酸苄酯 、 trans-4-amino-tetrahydrothiophen-3-ol 1,1-dioxide 生成 1-benzyl-3-[(3R,4R)-4-hydroxy-1,1-dioxothiolan-3-yl]thiourea
  参考文献：
  名称：

  缩合硫烷1,1-二氧化体系

  摘要：

  DOI：

  10.1007/bf00473338
• 作为产物：
  描述：

  3,4-环氧四氢噻吩-1,1-二氧化物 在 ammonium hydroxide 作用下， 反应 0.5h， 以65%的产率得到trans-4-amino-tetrahydrothiophen-3-ol 1,1-dioxide
  参考文献：
  名称：

  Structure–activity studies of cyclic ketone inhibitors of the serine protease plasmin: Design, synthesis, and biological activity

  摘要：

  Three series of cyclic ketone inhibitors were synthesized and evaluated against the serine protease plasmin. Peptide inhibitors that incorporated 3-oxotetrahydrofuran and 3-oxotetrahydrothiophene 1,1-dioxide groups had the highest activities. Alkylamino substituents, which were designed to bind in the S1 subsite of plasmin, were attached to the inhibitors. Compounds 5c and 5g, which incorporated 6-aminohexyl substituents, were found to be optimal and demonstrated IC50 values in the low micromolar range. Incorporating conformationally constrained peptide segments into the inhibitors did not improve their activities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.08.040

文献信息

• SUBSTITUTED PYRAZOLOPYRIMIDINES AS IRAK4 INHIBITORS
  申请人：Bayer AG

  公开号：EP3800188A1

  公开（公告）日：2021-04-07

  The present application relates to novel pyrazolopyrimidine derivatives for treatment and/or prophylaxis of diseases and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases in humans and in animals, especially of proliferative disorders, autoimmune disorders, metabolic and inflammatory disorders characterized by an overreacting immune system, in particular rheumatological disorders, inflammatory skin disorders, cardiovascular disorders, lung disorders, eye disorders, neurological disorders, pain disorders and cancer, in human as well as of allergic and/or inflammatory diseases in animals, especially of atopic dermatitis and/or Flea Allergy Dermatitis, and especially in domestic animals, particularly in dogs.

  本申请涉及用于治疗和/或预防疾病的新的吡唑并嘧啶衍生物，以及将它们用于生产用于治疗和/或预防人类和动物疾病的药物，尤其是增殖性疾病、自身免疫性疾病、代谢和炎症性疾病，这些疾病的特点是免疫系统过度反应，特别是风湿性疾病、炎症性皮肤病、心血管疾病、肺部疾病、眼病、神经系统疾病、疼痛疾病和癌症，在人类中，以及动物的过敏性/或炎症性疾病，特别是异位性皮炎和/或跳蚤过敏性皮炎，尤其是在家养动物中，特别是在狗中。
• 10.1016/j.molstruc.2024.139166
  作者：Zarovnaya, Iryna S.、Shishkina, Svitlana V.、Palchykov, Vitalii A.

  DOI：10.1016/j.molstruc.2024.139166

  日期：——

  reaction of - and -amino alcohols with aromatic aldehydes. An extensive spectroscopic characterization of the products, using 1D and 2D NMR techniques (H, C, NOE, NOESY, COSY, HSQC, HMBC) showed ring-chain tautomerism in deuterochloroform solution for -hydroxyimines. The content of the cyclic (1,3-oxazolidine) form increases with increasing electron-withdrawing strength of the substituent in the para position

  环砜及其衍生物在生物、制药、医药等诸多领域有着广泛的应用。在此，我们报道了通过-和-氨基醇与芳香醛反应合成了十种带有环丁砜部分的新羟基亚胺。使用 1D 和 2D NMR 技术（1H、13C、NOE、NOESY、COSY、HSQC、HMBC）对产物进行了广泛的光谱表征，结果显示在氘代氯仿溶液中，β-肟胺存在环链互变异构现象。环状(1,3-恶唑烷)形式的含量随着亚胺苯环对位取代基吸电子强度的增加而增加。使用XRD分析证实了-(3,4)-3-羟基-4-(()-(2-羟基亚苄基)氨基)四氢噻吩1,1-二氧化物的结构。此外，对产品的ADMET特性进行了评估，显示出较高的药物相似性。
• A study of the conditions of the formation of the cis and trans isomers of N-substituted 4-aminothiolan-3-ol 1,1-dioxides
  作者：T. �. Bezmenova、P. G. Dul'nev、M. V. Rybakova

  DOI：10.1007/bf00552774

  日期：1980.4
• Prochazka; Horak, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 2278,2281
  作者：Prochazka、Horak

  DOI：——

  日期：——
• Notes: Epoxidation of Butadiene Sulfone
  作者：Wayne Sorenson

  DOI：10.1021/jo01093a612

  日期：1959.11