12H-Benzophenothiazine-6,11-dione | 169775-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 12H-Benzophenothiazine-6,11-dione
• 英文别名: Benzophenothiazin-6,11-chinon；benzo[b]phenothiazine-6,11(12H)-dione；11H-benzo[b]phenothiazine-6,11(12H)-dione；6H-benzo[b]phenothiazine-6,11(12H)-dione；12H-benzo[b]phenothiazine-6,11-dione；12H-Benzo[b]phenothiazin-6,11-dion；12H-benzo[b]phenothiazine-6,11-dione
• CAS: 169775-34-2
• 化学式: C₁₆H₉NO₂S
• 分子量: 279.319
• InChiKey: JEKDXFOWQKFUTN-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  424.9±45.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12H-Benzophenothiazine-6,11-dione 生成 6-Ethoxy-benzophenothiazin-11-on
  参考文献：
  名称：

  Chinoniminiumsalze und Aminochinomethide

  摘要：

  DOI：

  10.1016/s0040-4039(00)88169-1
• 作为产物：
  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

文献信息

• Micelles catalyzed one pot regio- and chemoselective synthesis of benzo[a]phenazines and naphtho[2,3-d]imidazoles ‘in H2O’
  作者：Vishnu K. Tandon、Manoj K. Verma、Hardesh K. Maurya、Sandeep Kumar

  DOI：10.1016/j.tetlet.2014.09.103

  日期：2014.11

  An efficient, novel, and concise one pot regio- and chemoselective synthesis of benzo[a]phenazines (4) and naphtho[2,3-d]imidazoles (8) has been accomplished in excellent yields by nucleophilic substitution reaction of 2,3-dichloro-1,4-naphthoquinone (1) with o-phenylenediamine (2) and benzamidines (7) respectively ‘in H2O’ using base and micelles (SDS) as catalyst. Analog reaction of 2,3-dichloro-1

  通过2,3的亲核取代反应，以优异的收率实现了高效，新颖，简洁的一锅区域和化学选择性合成苯并[ a ]吩嗪（4）和萘并[2,3- d ]咪唑（8）。 -二氯-1,4-萘醌（1）与邻苯二胺（2）和联am（7）分别在碱和胶束（SDS）的催化下在H 2 O中形成。在相同条件下2,3-二氯-1,4-萘醌（1）与2-氨基苯硫酚（9）的模拟反应导致形成苯并[ b]的混合物]吩噻嗪（10），苯并[ a ]吩噻嗪（11）和苯并[ a ] -1,4-苯并噻嗪基-3,2-吩噻嗪（12）的产率分别为17％，23％和57％。
• Visible Light-Mediated Thiolation of Substituted 1,4-Naphthoquinones Using Eosin Y as a Photoredox Catalyst
  作者：Bhawana Nagar、Basab Bijayi Dhar

  DOI：10.1021/acs.joc.1c02924

  日期：2022.3.4

  (isolated yield of ≥75%) for thiolation of substituted 1,4-naphthoquinones using various aromatic and aliphatic thiols at room temperature is described herein. The rate-determining step of the reaction is thiyl radical generation, and the radical was characterized by high-resolution mass spectrometry. Cost effectiveness, operational simplicity, a short reaction time, high atom economy, and a very good yield

  在伊红 Y 存在下，本文描述了在室温下使用各种芳香族和脂肪族硫醇对取代的 1,4-萘醌进行硫醇化的可见光诱导的一步程序（分离产率≥75%）。该反应的限速步骤是硫自由基的产生，该自由基通过高分辨质谱进行表征。成本效益、操作简单、反应时间短、原子经济性高和非常好的产率使得这种光氧化还原介导的过程成为过渡金属（例如，Cu、Ag 和 Pd）催化的醌与硫醇或二硫化物。
• 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.
• Synthesis and Characterization of Novel Donor-Acceptor Naphthoquinone Derivatives with Photoinduced Charge-Transfer Properties. A Joint Experimental and Theoretical Study
  作者：Beatriz Illescas、Nazario Martin、Jose L. Segura、C. Seoane、Enrique Orti、Pedro M. Viruela、Rafael Viruela

  DOI：10.1021/jo00122a054

  日期：1995.9

  The synthesis of substituted benzo[b]phenoxazine-6,11-diones (7a-d) and their precursor N-tosyl derivatives (6a-d) is reported. The N-methylbenzo[b]phenoxazine-6,11-dione (8) and the analogous benzo[b]phenothiazine-6,11-dione (9) are also prepared. The UV-vis spectra of compounds 6, 7, and 9 show the existence of an intramolecular electronic transfer from the respective benzoxazine or benzothiazine donor fragments to the acceptor p-benzoquinone moiety. In agreement with this donor-acceptor character, the cyclic voltammograms of 7-9 exhibit two one-electron reduction waves to the corresponding radical-anion and dianion and two quasireversible oxidation peaks; however, the tosyl group in compounds 6 results in only one quasireversible oxidation wave at higher positive values. This causes a strong hypsochromic shift of the low-energy charge-transfer band. The molecular and electronic structures of compounds 6-8 are investigated using the semiempirical PM3 method and the nonempirical VEH approach, respectively. PM3 calculations predict that both the neutral and the reduced/oxidized compounds are nonplanar, the largest distortions from planarity being found for the most hindered N-tosylated derivatives 6. VEH calculations are used to rationalize the redox potentials and justify the low oxidation potentials measured for compounds 7 and 8. They also show the charge-transfer nature of the lowest-energy HOMO --> LUMO electronic transition, thus supporting the experimental UV-vis results. The higher oxidation potentials and blue-shifted absorption bands observed for compounds 6 are due to their highly distorted geometries which lead to a stabilization of the HOMO and a destabilization of the resulting cation-radical.
• Polynuclear Heterocycles. I. 1H-Benzo[b]pyrido[1,2,3-mn]phenoxazin-1-one and Related Substances^1a
  作者：J. A. VanAllan、G. A. Reynolds、R. E. Adel

  DOI：10.1021/jo01052a042

  日期：1962.5