isothiazolo[5,4-b]benzo[b]thiophene | 74313-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: isothiazolo[5,4-b]benzo[b]thiophene
• 英文别名: (1)benzothieno(3,2-d)isothiazole；[1]Benzothiolo[3,2-d][1,2]thiazole
• CAS: 74313-25-0
• 化学式: C₉H₅NS₂
• 分子量: 191.277
• InChiKey: BOVRAKLQBFHTLI-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  264.9±22.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isothiazolo[5,4-b]benzo[b]thiophene 、 甲基锂 生成 lithium;3-cyano-1-benzothiophene-2-thiolate
  参考文献：
  名称：

  ONYAMHOKO, N. V.;WEBER, R.;FAUCONNIER, A.;RENSON, M., BULL. SOC. CHIM. BELG., 1983, 92, N 1, 53-60

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲醛苯并噻吩 在 硫氰酸铵 、 叔丁基锂 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 6.5h， 生成 isothiazolo[5,4-b]benzo[b]thiophene
  参考文献：
  名称：

  Design, synthesis, and antifungal activity of inhibitors of brassilexin detoxification in the plant pathogenic fungus Leptosphaeria maculans

  摘要：

  Potential inhibitors of Leptosphaeria maculans mediated detoxification of the phytoalexin brassilexin were designed and synthesized based on the planar heteroaromatic structure of isothiazolo[5,4-b]indole. Screening of these compounds for inhibition of brassilexin detoxification in cultures of L. maculans indicated that 4-(2-chlorophenyl)isothiazole had the largest effect on the rate of brassilexin detoxification. However, the most antifungal compound among the potential inhibitors, isothiazolo[5,4-b]quinoline, did not appear to affect the metabolism of brassilexin noticeably, suggesting that growth inhibition is not sufficient to slow down the rate of brassilexin detoxification. Furthermore, it was determined that 4-arylisothiazoles as well as isothiazolo[5,4-b]thianaphthene displayed antifungal activity against L. maculans. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.053

文献信息

• Onyamboko, N. V.; Weber, R.; Fauconnier, A., Bulletin des Societes Chimiques Belges, 1983, vol. 92, # 1, p. 53 - 60
  作者：Onyamboko, N. V.、Weber, R.、Fauconnier, A.、Renson, M.

  DOI：——

  日期：——
• Design, synthesis, and antifungal activity of inhibitors of brassilexin detoxification in the plant pathogenic fungus Leptosphaeria maculans
  作者：M. Soledade. C. Pedras、Mojmir Suchy

  DOI：10.1016/j.bmc.2005.08.053

  日期：2006.2

  Potential inhibitors of Leptosphaeria maculans mediated detoxification of the phytoalexin brassilexin were designed and synthesized based on the planar heteroaromatic structure of isothiazolo[5,4-b]indole. Screening of these compounds for inhibition of brassilexin detoxification in cultures of L. maculans indicated that 4-(2-chlorophenyl)isothiazole had the largest effect on the rate of brassilexin detoxification. However, the most antifungal compound among the potential inhibitors, isothiazolo[5,4-b]quinoline, did not appear to affect the metabolism of brassilexin noticeably, suggesting that growth inhibition is not sufficient to slow down the rate of brassilexin detoxification. Furthermore, it was determined that 4-arylisothiazoles as well as isothiazolo[5,4-b]thianaphthene displayed antifungal activity against L. maculans. (c) 2005 Elsevier Ltd. All rights reserved.
• ONYAMHOKO, N. V.;WEBER, R.;FAUCONNIER, A.;RENSON, M., BULL. SOC. CHIM. BELG., 1983, 92, N 1, 53-60
  作者：ONYAMHOKO, N. V.、WEBER, R.、FAUCONNIER, A.、RENSON, M.

  DOI：——

  日期：——