2-chloro-3-(3-methoxy)phenylsulfanyl-[1,4]naphthoquinone | 1146961-25-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-(3-methoxy)phenylsulfanyl-[1,4]naphthoquinone
• 英文别名: 2-Chloro-3-(3-methoxyphenyl)sulfanylnaphthalene-1,4-dione
• CAS: 1146961-25-2
• 化学式: C₁₇H₁₁ClO₃S
• 分子量: 330.792
• InChiKey: MGBKCWLABNBRFR-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C(Solvent: Ethyl acetate; Hexane)
• 沸点：
  450.8±45.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-3-(3-methoxy)phenylsulfanyl-[1,4]naphthoquinone 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以79%的产率得到3-methoxy-6H-benzo[b]phenothiazine-6,11(12H)-dione
  参考文献：
  名称：

  2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: Synthesis and Biological evaluation as potential antiproliferative and antifungal agents

  摘要：

  A series of 2-chloro-3-arylsulfanyl-[1,4]naphthoquinones (2), 2,3-bis-arylsulfanyl-[1,4]naphthoquinones (3) and 12H-benzo[b]phenothiazine-6,11-diones and their analogs 6-8 were synthesized and evaluated for their antiproliferative activity against human cervical cancer (HeLa) cells. Compounds 3a and 3b were found to possess most potent antiproliferative and cell killing ability. Compounds 1-8 were also evaluated for antifungal activities. The structure-activity relationship of these compounds was studied and the results show that compound 2a (MIC50 = 1.56 mu g/mL) exhibited in vitro potent antifungal activity compared to the clinically useful antifungal. drug Fluconazole (MIC50 = 2.0 mu g/mL) against Sporothrix. schenckii. Compound 2a (MIC50 = 1.56 mu g/mL) also exhibited same antifungal activity compared to clinically useful drug Amphotericin-B (MIC50 = 1.56 mu g/mL) against Trichophyton. mentagraphytes. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.06.025
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 3-甲氧基苯硫酚 以 乙醇 为溶剂， 以63%的产率得到2-chloro-3-(3-methoxy)phenylsulfanyl-[1,4]naphthoquinone
  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.
• 2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: Synthesis and Biological evaluation as potential antiproliferative and antifungal agents
  作者：Vishnu K. Tandon、Hardesh K. Maurya、Ashutosh Tripathi、G.B. ShivaKeshava、Praveen K. Shukla、Pallavi Srivastava、Dulal Panda

  DOI：10.1016/j.ejmech.2008.06.025

  日期：2009.3

  A series of 2-chloro-3-arylsulfanyl-[1,4]naphthoquinones (2), 2,3-bis-arylsulfanyl-[1,4]naphthoquinones (3) and 12H-benzo[b]phenothiazine-6,11-diones and their analogs 6-8 were synthesized and evaluated for their antiproliferative activity against human cervical cancer (HeLa) cells. Compounds 3a and 3b were found to possess most potent antiproliferative and cell killing ability. Compounds 1-8 were also evaluated for antifungal activities. The structure-activity relationship of these compounds was studied and the results show that compound 2a (MIC50 = 1.56 mu g/mL) exhibited in vitro potent antifungal activity compared to the clinically useful antifungal. drug Fluconazole (MIC50 = 2.0 mu g/mL) against Sporothrix. schenckii. Compound 2a (MIC50 = 1.56 mu g/mL) also exhibited same antifungal activity compared to clinically useful drug Amphotericin-B (MIC50 = 1.56 mu g/mL) against Trichophyton. mentagraphytes. (C) 2008 Elsevier Masson SAS. All rights reserved.