4-chloro-2-(methylsulfanyl)-1,3-thiazole-5-carbonitrile | 120891-11-4

• 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-chloro-2-(methylsulfanyl)-1,3-thiazole-5-carbonitrile
• 英文别名: 4-chloro-2-methylthiothiazole-5-carbonitrile；2-methylthio-4-chloro-5-cyanothiazole；4-chloro-2-methylsulfanyl-1,3-thiazole-5-carbonitrile
• CAS: 120891-11-4
• 化学式: C₅H₃ClN₂S₂
• 分子量: 190.677
• InChiKey: HMVZRZHCGGGPFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-2-(methylsulfanyl)-1,3-thiazole-5-carbonitrile 在 sodium ethanolate 、 乙酸酐 、 三氯氧磷 作用下， 生成 5-Chloro-2-methylsulfanyl-thiazolo[5',4':4,5]thieno[3,2-d]pyrimidine
  参考文献：
  名称：

  Azoles。第10部分。噻唑并[4'，5'，4,5]噻吩并[3,2- d ]嘧啶，一种新的杂环系统

  摘要：

  通过使4-氯噻唑-5-甲醛或4-氯噻唑-5-腈与2-巯基乙酸乙酯或2-巯基乙酰胺反应来制备噻吩并[2,3- d ]噻唑。将获得的6-氨基噻吩并[2,3- d ]噻唑-5-羧酰胺转化为相应的噻唑并[4'，5'; 4,5]噻吩并[3,2 - d ]嘧啶-5（6 H）-一种通过在乙酸酐中用原甲酸三乙酯处理。用磷酰氯得到5-氯衍生物，当其与各种胺反应时，该氯原子被氯原子取代。5-氯噻唑并[4'，5'; 4,5]噻吩并[3,2- d ]-嘧啶的还原脱氯反应得到母体杂环。

  DOI：

  10.1016/s0040-4020(01)90380-1
• 作为产物：
  描述：

  4-氨基-2-甲基硫代噻唑-5-甲腈 在 亚硝酸特丁酯 、 copper dichloride 作用下， 以 乙腈 为溶剂， 以83%的产率得到4-chloro-2-(methylsulfanyl)-1,3-thiazole-5-carbonitrile
  参考文献：
  名称：

  4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K+-ATPase and Ras oncogene activity in cancer cells

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.01.046

文献信息

• New thiazole compounds having fungicidal activity
  申请人：Duphar International Research B.V.

  公开号：US04889863A1

  公开（公告）日：1989-12-26

  The invention relates to new thiazole compounds of the general formula ##STR1## wherein R is an C.sub.1 -C.sub.12 alkyl group or a phenyl group, which groups are unsubstituted or substituted with halogen, nitro or cyano; R.sub.1 is a cyano group; a formyl group; an alkylcarbonyl or alkoxycarbonyl group having 2-5 carbon atoms; or a substituted or non-substituted benzoyl group; R.sub.2 is a hydrogen atom; a halogen atom; an amino group; an amino group substituted with 1 or 2 substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 alkynyl, C.sub.2 -C.sub.5 alkylcarbonyl and C.sub.2 -C.sub.5 alkoxycarbonyl; an alkyl, alkoxy, alkylthio, alkylsulphinyl or alkyl-sulphonyl group having 1-4 carbon atoms; or a substituted or non-substituted aryl, aryloxy, arylthio, arylsulphinyl or arylsulphonyl group; and n is 1 or 2. The new compounds show a fungicidal activity and may be used in particular against plant pathogenic seed fungi and soil fungi.

  本发明涉及一种新的噻唑化合物，其通式为##STR1##其中，R是C.sub.1-C.sub.12烷基或苯基，这些基团未被卤素、硝基或氰基取代或被取代；R.sub.1是氰基；甲酰基；具有2-5个碳原子的烷基羰基或烷氧羰基基团；或被取代或未被取代的苯甲酰基团；R.sub.2是氢原子；卤素原子；氨基团；被1或2个从C.sub.1-C.sub.4烷基、C.sub.2-C.sub.5炔基、C.sub.2-C.sub.5烷基羰基和C.sub.2-C.sub.5烷氧羰基组成的取代基取代的氨基团；具有1-4个碳原子的烷基、烷氧基、烷硫基、烷基磺酰基或烷基磺酸基；或被取代或未被取代的芳基、芳氧基、芳硫基、芳基磺酰基或芳基磺酸基；n为1或2。这些新化合物表现出杀真菌活性，特别是对植物病原菌和土壤真菌具有杀菌作用。
• Thiazole compounds having fungicidal activity
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0301613B1

  公开（公告）日：1991-07-10
• US4889863A
  申请人：——

  公开号：US4889863A

  公开（公告）日：1989-12-26
• Azoles. Part 10. Thiazolo[4′,5′,4,5]thieno[3,2-d]pyrimidine, a New Heterocyclic Ring System
  作者：Salah Athmani、Brian Iddon

  DOI：10.1016/s0040-4020(01)90380-1

  日期：1992.9

  obtained were converted into the corresponding thiazolo[4′,5′;4,5]thieno[3,2-d]pyrimidin-5(6H)-one by treatment with triethyl orthoformate in acetic anhydride. With phosphoryl chloride these gave the 5-chloro-derivative, which underwent displacement of the chlorine-atom when allowed to react with various amines. Reductive dechlorination of 5-chlorothiazolo[4′,5′;4,5]thieno[3,2-d]-pyrimidine gave the parent

  通过使4-氯噻唑-5-甲醛或4-氯噻唑-5-腈与2-巯基乙酸乙酯或2-巯基乙酰胺反应来制备噻吩并[2,3- d ]噻唑。将获得的6-氨基噻吩并[2,3- d ]噻唑-5-羧酰胺转化为相应的噻唑并[4'，5'; 4,5]噻吩并[3,2 - d ]嘧啶-5（6 H）-一种通过在乙酸酐中用原甲酸三乙酯处理。用磷酰氯得到5-氯衍生物，当其与各种胺反应时，该氯原子被氯原子取代。5-氯噻唑并[4'，5'; 4,5]噻吩并[3,2- d ]-嘧啶的还原脱氯反应得到母体杂环。
• 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.