[Amino(quinolin-2-ylmethylsulfanyl)methylidene]azanium;chloride | 1822-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: [Amino(quinolin-2-ylmethylsulfanyl)methylidene]azanium;chloride
• 英文别名: [amino(quinolin-2-ylmethylsulfanyl)methylidene]azanium;chloride
• CAS: 1822-58-8；82081-43-4
• 化学式: C₁₁H₁₁N₃S*2ClH
• 分子量: 290.216
• InChiKey: CNPCHLPCXHAXIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  88.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [Amino(quinolin-2-ylmethylsulfanyl)methylidene]azanium;chloride 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 2-(tetrahydrothiophen-2-yl)quinoline
  参考文献：
  名称：

  Synthesis and antisecretory and antiulcer activities of derivatives and analogs of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide

  摘要：

  New thioamide derivatives of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (29) and related compounds (in which the tetrahydrothiophene ring was replaced by tetrahydrothiopyran, tetrahydrofuran, 1,3-dithiane, or 1,3-oxathiane and where the pyridine ring was replaced by other nitrogen heterocycles) were synthesized and tested for their antisecretory and antiulcer activities. These thioamides were prepared according to one of the following methods: reaction of an isothiocyanate with the carbanion of the corresponding cyclic precursor (for secondary thioamides); reaction of ammonia or an amine with the dithio ester prepared from the same precursor (for primary, secondary, and tertiary thioamides). These thioamides were evaluated by the Shay method to measure their antisecretory activity and by the stress-induced-ulcer method to test their antiulcer activity. Structure-activity relationships are discussed. N-Methyl-2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (R.P. 40749, 30) exhibited activities that were at least 10 times higher than those reported for cimetidine.

  DOI：

  10.1021/jm00384a004
• 作为产物：
  描述：

  2-氯甲基喹啉盐酸盐 、 硫脲 以 水 、 乙醇 为溶剂， 反应 3.0h， 以34%的产率得到[Amino(quinolin-2-ylmethylsulfanyl)methylidene]azanium;chloride
  参考文献：
  名称：

  新型硒代和硫脲衍生物对多种癌细胞具有强大的体外活性

  摘要：

  合成了一系列新型硒硒衍生物和相应的硫脲类似物，并针对六种人类癌细胞系进行了测试：黑色素瘤（1205Lu），肺癌（A549），前列腺癌（DU145），结直肠癌（HCT116），胰腺上皮样癌（PANC-1）和胰腺腺癌（BxPC3）。总的来说，我们发现含硒的衍生物比等规硫类似物更有效。四个硒硒衍生物（1e，1f，1g和1i）在72 h的所有测试细胞系中的IC 50值均低于10μM。根据其有效活性，化合物1g选择在不同结肠癌细胞系中进行进一步的生物学评估。我们的结果表明，化合物1g通过半胱天冬酶激活诱导细胞凋亡，同时抑制抗凋亡蛋白。

  DOI：

  10.1016/j.ejmech.2016.02.042

文献信息

• Horiuchi, Jiro; Suzuki, Kazuo; Shitara, Eiki, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 4, p. 1080 - 1084
  作者：Horiuchi, Jiro、Suzuki, Kazuo、Shitara, Eiki、Niwa, Ryuji、Kato, Tetsuzo

  DOI：——

  日期：——
• Synthesis and antisecretory and antiulcer activities of derivatives and analogs of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide
  作者：Jean-Claude Aloup、Jean Bouchaudon、Daniel Farge、Claude James、Jean Deregnaucourt、Monique Hardy-Houis

  DOI：10.1021/jm00384a004

  日期：1987.1

  New thioamide derivatives of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (29) and related compounds (in which the tetrahydrothiophene ring was replaced by tetrahydrothiopyran, tetrahydrofuran, 1,3-dithiane, or 1,3-oxathiane and where the pyridine ring was replaced by other nitrogen heterocycles) were synthesized and tested for their antisecretory and antiulcer activities. These thioamides were prepared according to one of the following methods: reaction of an isothiocyanate with the carbanion of the corresponding cyclic precursor (for secondary thioamides); reaction of ammonia or an amine with the dithio ester prepared from the same precursor (for primary, secondary, and tertiary thioamides). These thioamides were evaluated by the Shay method to measure their antisecretory activity and by the stress-induced-ulcer method to test their antiulcer activity. Structure-activity relationships are discussed. N-Methyl-2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (R.P. 40749, 30) exhibited activities that were at least 10 times higher than those reported for cimetidine.
• Novel seleno- and thio-urea derivatives with potent in vitro activities against several cancer cell lines
  作者：Verónica Alcolea、Daniel Plano、Deepkamal N. Karelia、Juan Antonio Palop、Shantu Amin、Carmen Sanmartín、Arun K. Sharma

  DOI：10.1016/j.ejmech.2016.02.042

  日期：2016.5

  potent than their isosteric sulfur analogs. Four selenourea derivatives (1e, 1f, 1g and 1i) showed IC50 values below 10 μM in all of tested cell lines at 72 h. On the basis of its potent activity, compound 1g was selected for further biological evaluation in different colon cancer cell lines. Our results indicated that compound 1g induced apoptosis by caspase activation, along with inhibition of anti-apoptotic

  合成了一系列新型硒硒衍生物和相应的硫脲类似物，并针对六种人类癌细胞系进行了测试：黑色素瘤（1205Lu），肺癌（A549），前列腺癌（DU145），结直肠癌（HCT116），胰腺上皮样癌（PANC-1）和胰腺腺癌（BxPC3）。总的来说，我们发现含硒的衍生物比等规硫类似物更有效。四个硒硒衍生物（1e，1f，1g和1i）在72 h的所有测试细胞系中的IC 50值均低于10μM。根据其有效活性，化合物1g选择在不同结肠癌细胞系中进行进一步的生物学评估。我们的结果表明，化合物1g通过半胱天冬酶激活诱导细胞凋亡，同时抑制抗凋亡蛋白。