4-amino-2-(1-pyrrolidinyl)-1,3-thiazole-5-carbonitrile | 68696-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-2-(1-pyrrolidinyl)-1,3-thiazole-5-carbonitrile
• 英文别名: 4-amino-2-pyrrolidin-1-yl-thiazole-5-carbonitrile；2-pyrrolidino-4-amino-5-cyanothiazole；4-Amino-2-(1-pyrrolidinyl)thiazol-5-carbonitril；4-amino-2-pyrrolidin-1-yl-1,3-thiazole-5-carbonitrile
• CAS: 68696-70-8
• 化学式: C₈H₁₀N₄S
• 分子量: 194.26
• InChiKey: FRCDSMLHJHGGAV-UHFFFAOYSA-N

物化性质

• 熔点：
  299 °C
• 沸点：
  415.6±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-2-(1-pyrrolidinyl)-1,3-thiazole-5-carbonitrile 在 盐酸 、 sodium nitrite 作用下， 以44%的产率得到4-chloro-6-(1-pyrrolidinyl)[1,3]thiazolo[4,5-d][1,2,3]triazine
  参考文献：
  名称：

  Synthesis of substituted [1,3]thiazolo[4,5-b]pyridines and [1,3]thiazolo[4,5-d][1,2,3]triazines

  摘要：

  In this work, we described an easy preparation Of substituted 4-amino-5-cyano-1,3-thiazoles. These compounds have been used as starting materials to obtain two classes of compounds. New substituted [1,3]thiazolo[4,5-e]pyridines were synthesized in one step via Friedlander reaction. Diazotation of 4-amino-5-cyano-1,3-thiazoles afforded 4-chloro[1,3]thiazolo[4,5-d][1,2,3]triazines in one step. The later Was substituted by a secondary amine to obtain substituted 4-amino[1,3]thiazolo[4,5-d][1,2,3]triazines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.017
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-amino-2-(1-pyrrolidinyl)-1,3-thiazole-5-carbonitrile
  参考文献：
  名称：

  Synthesis of substituted [1,3]thiazolo[4,5-b]pyridines and [1,3]thiazolo[4,5-d][1,2,3]triazines

  摘要：

  In this work, we described an easy preparation Of substituted 4-amino-5-cyano-1,3-thiazoles. These compounds have been used as starting materials to obtain two classes of compounds. New substituted [1,3]thiazolo[4,5-e]pyridines were synthesized in one step via Friedlander reaction. Diazotation of 4-amino-5-cyano-1,3-thiazoles afforded 4-chloro[1,3]thiazolo[4,5-d][1,2,3]triazines in one step. The later Was substituted by a secondary amine to obtain substituted 4-amino[1,3]thiazolo[4,5-d][1,2,3]triazines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.017

文献信息

• One-pot synthesis of new 2,4,5-trisubstituted 1,3-thiazoles and 1,3-selenazoles
  作者：David Thomae、Enrico Perspicace、Zhanjie Xu、Dorothée Henryon、Serge Schneider、Stéphanie Hesse、Gilbert Kirsch、Pierre Seck

  DOI：10.1016/j.tet.2009.01.104

  日期：2009.4

  In this work, we describe the synthesis of new 2,4,5-trisubstituted-1,3-thiazoles and 1,3-selenazole achieved by an easy one-pot four-step procedure. Expected compounds were obtained in good yield from dimethyl cyanodithioimidocarbonate, which was the common starting material for the preparation of all 1,3-thiazoles and 1,3-selenazoles. Chemical diversity was introduced on thiazole and selenazole rings

  在这项工作中，我们描述了通过简单的一锅四步法实现的新2,4,5-三取代-1,3-噻唑和1,3-硒唑的合成。从氰基二硫代亚氨基碳酸二甲酯中可以以高收率获得预期的化合物，后者是制备所有1,3-噻唑和1,3-硒唑的常用原料。通过改变所用的胺和活化的卤化物，在噻唑和硒唑环上引入了化学多样性。
• Process for the production of 4,5-disubstituted thiazoles
  申请人：BASF Aktiengesellschaft

  公开号：US04153607A1

  公开（公告）日：1979-05-08

  4,5-Disubstituted thiazoles are manufactured by reacting 4-amino-5-cyano-thiazoles with hydrogen sulfide in the presence of basic compounds, followed by dehydrogenating cyclization. The new 3-amino-thiazolo-(4,5-c)-isothiazoles I, 4-amino-5-thiocarbamidothiazoles III and 4,5-disubstituted thiazoles IV obtainable by the process of the invention are valuable intermediates for the manufacture of azo dyes and of crop protection agents.

  4,5-二取代噻唑是通过在碱性化合物存在下，将4-氨基-5-氰基噻唑与氢硫化物反应，然后进行脱氢环化制造的。本发明的新型3-氨基噻唑并[4,5-c]异噻唑酮I，4-氨基-5-硫代氨基噻唑III和4,5-二取代噻唑IV是制造偶氮染料和作物保护剂的有价值的中间体。
• 4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K+-ATPase and Ras oncogene activity in cancer cells
  作者：Florence Lefranc、Zhanjie Xu、Patricia Burth、Véronique Mathieu、Germain Revelant、Mauro Velho de Castro Faria、Caroline Noyon、Diogo Gomes Garcia、Damien Dufour、Céline Bruyère、Cassiano Felippe Gonçalves-de-Albuquerque、Pierre Van Antwerpen、Bernard Rogister、Stéphanie Hesse、Gilbert Kirsch、Robert Kiss

  DOI：10.1016/j.ejmech.2013.01.046

  日期：2013.5

  The in vitro growth inhibitory activity of 26 thiazoles (including 4-halogeno-2,5-disubtituted-1,3-thiazoles) and 5 thienothiazoles was assessed on a panel of 6 human cancer cell lines, including glioma cell lines. (4-Chloro-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12a) and (4-bromo-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12b) displayed similar to 10 times greater in vitro growth inhibitory activity than perillyl alcohol (POH), which therapeutically benefits glioma patients through the inhibition of both alpha-1 Na+/K+-ATPase (NAK) and Ras oncogene activity. The in vitro cytostatic activities (as revealed by quantitative videomicroscopy) displayed by 12a and 12b were independent of the intrinsic resistance to pro-apoptotic stimuli associated with cancer cells. Compounds 12a and 12b displayed relatively similar inhibitory activities on purified guinea pig brain preparations that mainly express NAK alpha-2 and alpha-3 subunits, whereas only compound 12b was efficacious against purified guinea pig kidney preparations that mainly express the NAK alpha-1 subunit, which is also expressed in gliomas, melanomas and non-small-cell lung cancers NSCLCs. (C) 2013 Elsevier Masson SAS. All rights reserved.
• SEYBOLD G.; EILINGSFELD H., LIEBIGS ANN. CHEM., 1979, NO 9, 1271-1279
  作者：SEYBOLD G.、 EILINGSFELD H.

  DOI：——

  日期：——
• US4153607A
  申请人：——

  公开号：US4153607A

  公开（公告）日：1979-05-08