3-benzyl-1,2,3,3a,4,5-hexahydrocanthin-6-one | 65284-99-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吲哚萘啶生物碱
• 英文名称: 3-benzyl-1,2,3,3a,4,5-hexahydrocanthin-6-one
• 英文别名: 6-Benzyl-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-9(16),10,12,14-tetraen-2-one
• CAS: 65284-99-3
• 化学式: C₂₁H₂₀N₂O
• 分子量: 316.403
• InChiKey: YLQAJRDUWMLQST-UHFFFAOYSA-N

物化性质

• 熔点：
  173.3-173.9 °C
• 沸点：
  480.9±33.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-1,2,3,3a,4,5-hexahydrocanthin-6-one 在 5%-palladium/activated carbon 、 甲酸铵 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.0h， 以72%的产率得到1,2,3,3a,4,5-六氢铁屎米酮
  参考文献：
  名称：

  铁屎米-6-酮季铵盐及其制备方法与应用

  摘要：

  本发明涉及一种铁屎米‑6‑酮季铵盐及其制备方法与应用。所涉及的化合物结构如式(I)所示，其中R为乙基、丙基、异丙基、烯丙基、正丁基、异丁基、正戊基、正辛基、非取代苄基或者，氢原子、甲基、溴甲基、三氟甲基、苄氧基、氟原子或氯原子取代的取代苄基；X为氯、溴或碘。所涉及的应用为上述化合物用于制备抗菌药物的应用。

  公开号：

  CN104530047B
• 作为产物：
  描述：

  苯甲醛 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 反应 85.0h， 生成 3-benzyl-1,2,3,3a,4,5-hexahydrocanthin-6-one
  参考文献：
  名称：

  Synthesis, in vitro antibacterial activities of a series of 3- N -substituted canthin-6-ones

  摘要：

  An improved synthetic route of canthin-6-one was accomplished. To further enhance the antibacterial potency and improve water solubility, a series of 3-N-alkylated and 3-N-benzylated canthin-6-ones were designed and synthesized, and their in vitro antibacterial activities were evaluated. A clear structure-activity relationship with peak minimal inhibitory concentration (MIC) values of 0.98 (mu g.mL(-1)) was investigated. Particularly, compounds 6i-r and 6t were found to be the most potent compounds with minimal inhibitory concentration (MIC) values lower than 1.95 (mu g.mL(-1)) against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.070

文献信息

• Shimizu, Masato; Ishikawa, Masayuki; Komoda, Yasuo, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 12, p. 4529 - 4533
  作者：Shimizu, Masato、Ishikawa, Masayuki、Komoda, Yasuo、Matsubara, Yukimi、Nakajima, Terumi

  DOI：——

  日期：——
• An Improved Synthesis of Canthin-6-one
  作者：Kevin M. Czerwinski、Craig A. Zificsak、John Stevens、Melissa Oberbeck、Christopher Randlett、Melissa King、Steve Mennen

  DOI：10.1081/scc-120017199

  日期：2003.1.5

  An improved route has been devised which provides canthin-6-one in the highest yield from tryptamine to date. Tryptamine is converted to N-b-benzyltryptamine via reaction with benzoylchloride and reduction using LAH. Pictet-Spengler condensation with 2-ketoglutaric acid, removal of the protecting group by CTH, and aromatization with MnO2 affords canthin-6-one in 48% overall yield.
• Selenium dioxide oxidations in the indole area. Synthesis of β-carboline alkaloids
  作者：M. Cain、O. Campos、F. Guzman、J. M. Cook

  DOI：10.1021/ja00342a045

  日期：1983.2
• Campos, Olivia; DiPierro, Mike; Cain, Michael, Heterocycles, 1980, vol. 14, # 7, p. 975 - 984
  作者：Campos, Olivia、DiPierro, Mike、Cain, Michael、Mantei, Robert、Gawish, Ali、Cook, James M.

  DOI：——

  日期：——
• Synthesis, in vitro antibacterial activities of a series of 3- N -substituted canthin-6-ones
  作者：Jiang-Kun Dai、Wen-Jia Dan、Na Li、Hong-Tao Du、Ji-Wen Zhang、Jun-Ru Wang

  DOI：10.1016/j.bmcl.2015.11.070

  日期：2016.1

  An improved synthetic route of canthin-6-one was accomplished. To further enhance the antibacterial potency and improve water solubility, a series of 3-N-alkylated and 3-N-benzylated canthin-6-ones were designed and synthesized, and their in vitro antibacterial activities were evaluated. A clear structure-activity relationship with peak minimal inhibitory concentration (MIC) values of 0.98 (mu g.mL(-1)) was investigated. Particularly, compounds 6i-r and 6t were found to be the most potent compounds with minimal inhibitory concentration (MIC) values lower than 1.95 (mu g.mL(-1)) against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.