3-Methyl-4-thiocarbamoyl-pyridin | 20970-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-Methyl-4-thiocarbamoyl-pyridin
• 英文别名: 3-Methylpyridine-4-carbothioamide
• CAS: 20970-78-9
• 化学式: C₇H₈N₂S
• 分子量: 152.22
• InChiKey: JYCGREAHQOKSHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-溴乙酰基)吡啶氢溴酸盐 、 3-Methyl-4-thiocarbamoyl-pyridin 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以56%的产率得到2-(3-methylpyridin-4-yl)-4-(pyridin-3-yl)thiazole
  参考文献：
  名称：

  Optimization of the aromatase inhibitory activities of pyridylthiazole analogues of resveratrol

  摘要：

  Aromatase is an established target not only for breast cancer chemotherapy, but also for breast cancer chemoprevention. The moderate and non-selective aromatase inhibitory activity of resveratrol (1) was improved about 100-fold by replacement of the ethylenic bridge with a thiadiazole and the phenyl rings with pyridines (e.g., compound 3). The aromatase inhibitory activity was enhanced over 6000-fold by using a 1,3-thiazole as the central ring and modifying the substituents on the 'A' ring to target the Met374 residue of aromatase. On the other hand, targeting the hydroxyl group of Thr310 by a hydrogen-bond acceptor on the 'B' ring did not improve the aromatase inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.047
• 作为产物：
  描述：

  3-甲基吡啶-4-甲酰胺 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以54%的产率得到3-Methyl-4-thiocarbamoyl-pyridin
  参考文献：
  名称：

  Optimization of the aromatase inhibitory activities of pyridylthiazole analogues of resveratrol

  摘要：

  Aromatase is an established target not only for breast cancer chemotherapy, but also for breast cancer chemoprevention. The moderate and non-selective aromatase inhibitory activity of resveratrol (1) was improved about 100-fold by replacement of the ethylenic bridge with a thiadiazole and the phenyl rings with pyridines (e.g., compound 3). The aromatase inhibitory activity was enhanced over 6000-fold by using a 1,3-thiazole as the central ring and modifying the substituents on the 'A' ring to target the Met374 residue of aromatase. On the other hand, targeting the hydroxyl group of Thr310 by a hydrogen-bond acceptor on the 'B' ring did not improve the aromatase inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.047

文献信息

• [EN] THIAZOLE DERIVATIVES<br/>[FR] DERIVES DE THIAZOLE
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1999015524A1

  公开（公告）日：1999-04-01

  (EN) Thiazole derivatives of formula (I) wherein R1 is amino; lower alkylamino; heterocyclic ring containing nitrogen which may be substituted with halogen(s), amino(s), N-oxide, lower alkoxy(s), lower alkyl(s), lower alkoxycarbonyl(s), halo(lower)-alkoxycarbonyl(s), cyano(s), cyclo(lower)alkylamino(s), lower alkylamino(s), heterocyclic ring containing nitrogen (s), or oxo; or lower alkyl substituted with heterocyclic ring containing nitrogen; R2 is hydrogen; hydroxy; lower alkyl; or lower alkoxy; R3 is hydrogen; lower alkyl which may be substituted with acyl(s), N-mono(or di)(lower)alkylamino(s), lower alkylthio(s), lower alkoxy(s), carboxy(s), heterocyclic ring containing nitrogen(s), lower alkynyl(s), halogen(s), or aryl(s); acyl; or cyclo(lower)alkyl; R2 and R3 may be linked together to form lower alkylene, R4 is hydrogen; lower alkyl; halogen; or lower alkylthio; X is lower alkylene which may be substituted with heterocyclic ring containing nitrogen(s), halogen(s), hydroxy(s), phenyl(lower)alkylidene(s), N-mono(or di)-(lower)alkylamino(lower)alkylidene(s), hydroxy(lower)alkylidene(s), or lower alkoxyimino(s); cyclo(lower)alkylidene; carbonyl; or thio; Y is lower alkylene which may be substituted with oxo, or thioxo; and X and Y may be linked together to form lower alkenylene, X and N are respectively bonded to the adjoining carbon atoms on the benzene ring, or a pharmaceutically acceptable salt thereof, which are useful as a medicament.(FR) L'invention concerne des dérivés de thiazole, ou leurs sels pharmaceutiquement acceptables, représentés par la formule (I). Dans ladite formule, R1 est amino; alkylamino inférieur; un anneau hétérocyclique contenant azote éventuellement substitué par halogène(s), amino(s), N-oxyde, alcoxy(s) inférieur(s), alkyle(s) inférieur(s), alcoxycarbonyle(s) inférieur(s), haloalcoxycarbonyle(s) (inférieur(s)), cyano(s), cycloalkylamino(s) (inférieur(s)), alkylamino(s) inférieur(s), un anneau hétérocyclique contenant azote(s), ou oxo; ou alkyle inférieur substitué par un anneau hétérocyclique contenant azote; R2 est hydrogène; hydroxy, alkyle inférieur; ou alcoxy inférieur; R3 est hydrogène; alkyle inférieur éventuellement substitué par acyle(s), N-mono (ou di)alkylamino(s) (inférieur(s)), alkylthio(s) inférieur(s) alcoxy(s) inférieur(s), carboxy(s), un anneau hétérocyclique contenant azote(s), alkynyle(s) inférieur(s), halogène(s), ou aryle(s); acyle; ou cycloalkyle inférieur; R2 et R3 peuvent être liés pour former alkylène inférieur, R4 est hydrogène; alkyle inférieur; halogène; ou alkylthio inférieur; X est alkylène inférieur éventuellement substitué par un anneau hétérocyclique contenant azote(s), halogène(s), hydroxy(s), phénylalkylidène(s) inférieur(s), N-mono (ou di)alkylamino (inférieur) alkylidène(s) (inférieur(s)), hydroxyalkylidène(s) (inférieur(s)), ou alcoxyimino(s) inférieur(s); cycloalkylidène (inférieur); carbonyle; ou thio; Y est alkylène inférieur éventuellement substitué par oxo, ou thioxo, et X et Y peuvent être liés pour former alcénylène inférieur, X et N étant respectivement liés aux atomes de carbone attenants sur le noyau benzénique. Les dérivés en question, ou leurs sels pharmaceutiquement acceptables, sont utiles comme médicaments.