2-mercapto-3-methoxybenzonitrile | 88791-24-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 2-mercapto-3-methoxybenzonitrile
• 英文别名: 3-methoxy-2-sulfanylbenzonitrile
• CAS: 88791-24-6
• 化学式: C₈H₇NOS
• 分子量: 165.216
• InChiKey: BIEFQCOTRGGUIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-mercapto-3-methoxybenzonitrile 在 ammonium hydroxide 、 sodium hypochlorite 作用下， 以 水 为溶剂， 反应 3.0h， 以73%的产率得到3-amino-7-methoxy-1,2-benzisothiazole
  参考文献：
  名称：

  Rahman, Loay K. A.; Scrowston, Richard M., Journal of the Chemical Society. Perkin transactions I, 1983, # 12, p. 2973 - 2978

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-3-甲氧基苯腈 在 盐酸 、 sodium hydroxide 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.42h， 生成 2-mercapto-3-methoxybenzonitrile
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2- and 3-Aminobenzo[b]thiophene Derivatives as Antimitotic Agents and Inhibitors of Tubulin Polymerization

  摘要：

  Two new series of inhibitors of tubulin polymerization based on the 2-amino-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene molecular skeleton and its 3-amino positional isomer were synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. Although many more 3-amino derivatives have been synthesized so far, the most promising compound in this series was 2-amino-6-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene, which inhibits cancer cell growth at subnanomolar concentrations and interacts strongly with tubulin by binding to the colchicine site.

  DOI：

  10.1021/jm070050f

文献信息

• RAHMAN, L. K. A.;SCROWSTON, R. M., J. CHEM. SOC. PERKIN TRANS., 1983, N 12, 2973-2977
  作者：RAHMAN, L. K. A.、SCROWSTON, R. M.

  DOI：——

  日期：——
• HETEROCYCLIC COMPOUNDS AND THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：EP0526588A1

  公开（公告）日：1993-02-10
• US5182279A
  申请人：——

  公开号：US5182279A

  公开（公告）日：1993-01-26
• [EN] HETEROCYCLIC COMPOUNDS AND THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：WO1991016325A1

  公开（公告）日：1991-10-31

  (EN) Novel [1]benzothieno[2,3-b]pyrazine-2,3(1H,4H)-diones or tautomeric forms thereof of general formula (I), wherein R1, R2, R3 and R4 independently represent hydrogen, halogen, alkyl, alkoxy or trifluoromethyl. The compounds are useful in the treatment of neurological and psychiatric diseases.(FR) On décrit de nouvelles [1]benzothiéno[2,3-b]pyrazine-2,3(1H,4H)-diones ou leurs formes tautomères ayant la formule générale (I), où R1, R2, R3 et R4 représentent indépendamment hydrogène, halogène, alkyle, alcoxy ou trifluorométhyle. Lesdits composés sont utiles dans le traitement de maladies neurologiques et psychiatriques.
• Synthesis and Biological Evaluation of 2- and 3-Aminobenzo[<i>b</i>]thiophene Derivatives as Antimitotic Agents and Inhibitors of Tubulin Polymerization
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Carlota Lopez Cara、Delia Preti、Francesca Fruttarolo、Maria Giovanna Pavani、Mojgan Aghazadeh Tabrizi、Manlio Tolomeo、Stefania Grimaudo、Antonella Di Cristina、Jan Balzarini、John A. Hadfield、Andrea Brancale、Ernest Hamel

  DOI：10.1021/jm070050f

  日期：2007.5.1

  Two new series of inhibitors of tubulin polymerization based on the 2-amino-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene molecular skeleton and its 3-amino positional isomer were synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. Although many more 3-amino derivatives have been synthesized so far, the most promising compound in this series was 2-amino-6-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene, which inhibits cancer cell growth at subnanomolar concentrations and interacts strongly with tubulin by binding to the colchicine site.