3-methoxy-12-phenyl-12,13-dihydrobenzo[f]naphtho[2,3-b][1,4]thiazepine-6,11-dione | 1171120-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-methoxy-12-phenyl-12,13-dihydrobenzo[f]naphtho[2,3-b][1,4]thiazepine-6,11-dione
• 英文别名: 3-methoxy-12-phenyl-13H-naphtho[3,2-b][1,4]benzothiazepine-6,11-dione
• CAS: 1171120-83-4
• 化学式: C₂₄H₁₇NO₃S
• 分子量: 399.47
• InChiKey: KLVATDYIFDZNOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 2-(3-methoxyphenylthio)-3-(phenylamino)naphthalene-1,4-dione 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到3-methoxy-12-phenyl-12,13-dihydrobenzo[f]naphtho[2,3-b][1,4]thiazepine-6,11-dione
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents

  摘要：

  A series of 2-Arylamino-3-chloro-1,4-naphthoquinones (3), 2-Amino-3-aryisulfanyl-1,4-naphthoquinones (5), 2-Arylamino-3-arylsulfanyl-1,4-naphthoquinones (6), Dihydrobenzo[f]naphtho[2,3-b][1,4]thiazelpine-6,11-diones (9) (via Pictet-Spengler cyclization), Isoindoline-1,3-dione derivatives of 1,4- naphthoquinone (13), 2,2'-(1,4-Dioxo-1,4-dihydronaphthalene-2,3-diyl)bis(methylene)dibenzonitrile (14), 13-Amino-12-substituted-6H-benzo[e]naphtho [2,3-b][1,4]diazepine-6,11(12H)-diones (15-16), 2-Chloro-3-atylsulfanyl-1,4-naphthoquinones (17-18) and 3-Methyl-6H-benzo[b]phenothiazine-6,11(12H)-dione (19) were synthesized and studied for their antifungal and antibacterial activities. The results indicate that compounds 3b, 5a and 5b have potent antifungal activity. Amongst the most promising antifungal compounds, 3b showed better antifungal activity than clinically prevalent antifungal drug Fluconazole (MIC50 = 2.0 mu g/mL) against Sporothrix schenckii (MIC50 = 1.56 mu g/mL), significant profile against Candida albicans (MIC50 = 1.56 mu g/mL), Cryptococcus neoformans (MIC50 = 0.78 mu g/mL) and Trichophyton mentagraphytes (MIC50 = 1.56 mu g/mL) and same antifungal activity when compared with Amphotericin-B against C. neoformans (MIC50 = 0.78 mu g/mL). Compounds 3b, 5a and 5b also showed promising antibacterial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.006

文献信息

• Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents
  作者：Vishnu K. Tandon、Hardesh K. Maurya、Nripendra N. Mishra、Praveen K. Shukla

  DOI：10.1016/j.ejmech.2009.03.006

  日期：2009.8

  A series of 2-Arylamino-3-chloro-1,4-naphthoquinones (3), 2-Amino-3-aryisulfanyl-1,4-naphthoquinones (5), 2-Arylamino-3-arylsulfanyl-1,4-naphthoquinones (6), Dihydrobenzo[f]naphtho[2,3-b][1,4]thiazelpine-6,11-diones (9) (via Pictet-Spengler cyclization), Isoindoline-1,3-dione derivatives of 1,4- naphthoquinone (13), 2,2'-(1,4-Dioxo-1,4-dihydronaphthalene-2,3-diyl)bis(methylene)dibenzonitrile (14), 13-Amino-12-substituted-6H-benzo[e]naphtho [2,3-b][1,4]diazepine-6,11(12H)-diones (15-16), 2-Chloro-3-atylsulfanyl-1,4-naphthoquinones (17-18) and 3-Methyl-6H-benzo[b]phenothiazine-6,11(12H)-dione (19) were synthesized and studied for their antifungal and antibacterial activities. The results indicate that compounds 3b, 5a and 5b have potent antifungal activity. Amongst the most promising antifungal compounds, 3b showed better antifungal activity than clinically prevalent antifungal drug Fluconazole (MIC50 = 2.0 mu g/mL) against Sporothrix schenckii (MIC50 = 1.56 mu g/mL), significant profile against Candida albicans (MIC50 = 1.56 mu g/mL), Cryptococcus neoformans (MIC50 = 0.78 mu g/mL) and Trichophyton mentagraphytes (MIC50 = 1.56 mu g/mL) and same antifungal activity when compared with Amphotericin-B against C. neoformans (MIC50 = 0.78 mu g/mL). Compounds 3b, 5a and 5b also showed promising antibacterial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.