2-chloro-3-phenylsulfanyl-[1,4]naphthoquinone | 101080-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-phenylsulfanyl-[1,4]naphthoquinone
• 英文别名: 2-chloro-3-thiophenyl-1,4-naphthoquinone；2-Chloro-3-phenylsulfanyl-naphthalene-1,4-dione；2-chloro-3-phenylsulfanylnaphthalene-1,4-dione
• CAS: 101080-89-1
• 化学式: C₁₆H₉ClO₂S
• 分子量: 300.765
• InChiKey: PZEJBCOFYTWHHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-3-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85%的产率得到12H-Benzophenothiazine-6,11-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-氯-1,4-萘醌 、 苯硫酚 在 aluminum oxide 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以90%的产率得到2-chloro-3-phenylsulfanyl-[1,4]naphthoquinone
  参考文献：
  名称：

  Kanodia, Saraswati; Thapliyal, Prakash Chander, Journal of the Indian Chemical Society, 2012, vol. 89, # 6, p. 833 - 836

  摘要：

  DOI：

文献信息

• ‘On water’: unprecedented nucleophilic substitution and addition reactions with 1,4-quinones in aqueous suspension
  作者：Vishnu K. Tandon、Hardesh K. Maurya

  DOI：10.1016/j.tetlet.2009.07.149

  日期：2009.10

  Unique nucleophilic substitution and addition reactions of 1,4-quinones in aqueous suspension with aromatic amines, primary aliphatic amines, amino acid, ester of amino acid, heterocyclic amines, hydrazine, amide, and thioethers are described in absence of catalyst against the traditional synthetic routes of these reactions in non-aqueous medium in presence of catalyst.

  在没有传统合成催化剂的催化剂的情况下，描述了水性悬浮液中1,4-醌与芳香胺，伯脂肪胺，氨基酸，氨基酸酯，杂环胺，肼，酰胺和硫醚的独特亲核取代和加成反应催化剂存在下在非水介质中进行这些反应的途径。
• [EN] NAPHTHAQUINONE METHYLTRANSFERASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE NAPHTAQUINONE MÉTHYLTRANSFÉRASE ET LEURS UTILISATIONS
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2015172076A1

  公开（公告）日：2015-11-12

  Provided herein are compounds of (I), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, and prodrugs thereof. Also provided are pharmaceutical compositions and methods involving the inventive compounds for the treatment of proliferative diseases (e.g., cancer (e.g., leukemia, breast cancer, melanoma, metastatic cancer) and diseases associated with inappropriate SET8 activity. Also provided are methods for inhibiting SET8 and methods for labelling SET8.

  本文提供了化合物(I)及其药用可接受的盐、溶剂合物、水合物、多型体、共晶体、互变异构体、立体异构体和其前药。还提供了涉及创新化合物用于治疗增殖性疾病（例如，癌症（例如，白血病、乳腺癌、黑色素瘤、转移性癌症）和与不当的SET8活性相关的疾病）的药物组合物和方法。还提供了用于抑制SET8的方法和用于标记SET8的方法。
• 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.
• Kanodia, Saraswati; Thapliyal, Prakash Chander, Journal of the Indian Chemical Society, 2012, vol. 89, # 6, p. 833 - 836
  作者：Kanodia, Saraswati、Thapliyal, Prakash Chander

  DOI：——

  日期：——