3,1-benzothiazin-2,4-dithione | 16081-97-3

• 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: 3,1-benzothiazin-2,4-dithione
• 英文别名: 2H-3,1-benzothiazine-2,4(1H)-dithione；1H-3,1-benzothiazine-2,4-dithione
• CAS: 16081-97-3
• 化学式: C₈H₅NS₃
• mdl: MFCD05855591
• 分子量: 211.332
• InChiKey: QIQQPMKEDZXZEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,1-benzothiazin-2,4-dithione 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 苯并咪唑并[1,2-c]喹唑啉-6(5H)-硫酮
  参考文献：
  名称：

  Leistner; Wagner; Strohscheidt Th., Pharmazie, 1980, vol. 35, # 5-6, p. 293 - 296

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氨基三氟甲苯 在 sodium sulfide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 3,1-benzothiazin-2,4-dithione
  参考文献：
  名称：

  Sulfurization of 2-aminobenzotrifluoride with sodium sulfide

  摘要：

  DOI：

  10.1021/jo00148a006

文献信息

• Reactions of 1,2‐dihydro‐4 <i>H</i> ‐3,1‐benzothiazine‐2,4‐dithiones (trithioisatoic anhydrides) with <i>N</i> ‐substituted benzylamines and trialkyl phosphites
  作者：Masahiko Takahashi、Tomoko Gunji、Akiko Ichikawa

  DOI：10.1002/jhet.5570390527

  日期：2002.9

  Reactions of 1,2-dihydro-4H-3,1-benzothiazine-2,4-dithiones (trithioisatoic anhydrides) 3 with N-substi-tuted benzylamines 9 gave 1,2-dihydroquinazoline-4-thiones 10, o-thioureidodithiobenzoic acid 11, o-aminothiobenzamides 12, 2-amino-3,1-benzothiazine-4-thiones 13, or quinazoline-2,4-dithiones 14, depending on the kinds of amine and the reaction solvent. On the other hand, reaction of 3 with trialkyl

  1,2-二氢-4 H -3,1-苯并噻嗪-2,4-二硫酮（三硫代脲酸酐）3与N-取代的苄胺9的反应得到1,2-二氢喹唑啉-4-硫酮10，邻硫脲二硫代苯甲酸酯酸11，直径： -aminothiobenzamides 12，2-氨基-3,1-苯并噻嗪-4-硫酮13，或喹唑啉-2,4- dithiones 14，这取决于种胺和反应溶剂。另一方面，3与亚磷酸三烷基酯的反应得到二烷基（1,2-二氢-2-thioxo-4 H -3,1-苯并噻嗪-4-基）膦酸酯18。
• Synthesis and cytotoxic activity against human tumor cells of heterocyclic systems derived from 2‐thioxo‐1,2‐dihydro‐4 <i>H</i> ‐3,1‐benzothazin‐4‐one
  作者：Tamer A. Khlosy、Marwa S. Salem、Amira T. Ali、Hassan M.F. Madkour

  DOI：10.1002/jhet.3745

  日期：2020.1

  were evaluated in vitro for their antiproliferative activity against HePG‐2 and MCF‐7 cell lines. 2H‐Benzo[d][1,3]thiazine‐2,4(1H)‐dithione and 2‐thioxo‐1,2‐dihydro‐4H‐benzo[d][1,3]thiazin‐4‐one were the most potent against the two cancer cells compared to that of the reference compound doxorubicin. Most of the synthesized compounds also exhibited good cytotoxic activity.

  制备了标题化合物，并转化为2-肼基-2-1,2-二氢-4 H-苯并[d] [1,3]噻嗪-4-酮，该化合物也用于合成稠合杂环系统，即苯并三唑并噻嗪酮衍生物。例如，通过与甲酰胺，乙酸，氰基乙酸乙酯，顺丁烯二酸酐和苯甲醛分别与甘氨酸处理，然后形成非稠合杂环体系，如吡唑基-苯并噻嗪酮，苯并噻嗪基哒嗪和咪唑基苯并噻嗪酮衍生物。所有化合物均已通过IR，MS和1 H-NMR光谱进行了结构表征。对合成的化合物进行了体外评估具有抗HePG-2和MCF-7细胞系的抗增殖活性。-2H-苯并[d] [1,3]噻嗪-2,4（1H）-dithione和2-硫代-1,2-二氢-4- ħ -苯并[d] [1,3]噻嗪-4-酮为与参考化合物阿霉素相比，对两种癌细胞最有效。大多数合成的化合物还表现出良好的细胞毒性活性。
• Direct Formation of Ring-Fused 1,3-Thiazine-2,4-dithiones from Aromatic <i>o</i>-Amino Carboxylic Acids: Observation of a Carbon Disulfide Mediated Thionation
  作者：Philipp A. Ottersbach、Paul W. Elsinghorst、Hans-Georg Häcker、Michael Gütschow

  DOI：10.1021/ol101471g

  日期：2010.8.20

  A facile synthesis of 2H-3,1-benzothiazine-2,4(1H)-dithiones (trithioisatoic anhydrides) or 2H-naphtho[2,3-d][1,3]thiazine-2,4(1H)-dithione solely from anthranilic acids or 3-amino-2-naphthoic acid and carbon disulfide, performed at room temperature in 1,4-dioxane in the presence of Et3N, is reported. Corresponding 2-alkylsulfanyl derivatives were obtained in one-pot reactions under the same conditions

  2 H -3,1-苯并噻嗪-2,4（1 H）-二硫酮（三硫代硬脂酸酐）或2 H-萘[2,3- d ] [1,3]噻嗪-2,4（1 ）的简便合成据报道，在室温下在Et 3 N存在下于1,4-二恶烷中进行的仅由邻氨基苯甲酸或3-氨基-2-萘甲酸和二硫化碳制得的H）-二硫酮。加入卤代烷后，在相同条件下，通过一锅法反应获得了相应的2-烷基硫烷基衍生物。使用13 C标记的二硫化碳研究了噻嗪环化的机理，结果表明二硫化碳被掺入杂环中并另外充当了硫磺化试剂。
• Analogues of the potential antipsychotic agent 1192U90: amide modifications
  作者：Frank Navas III、Flora L.M. Tang、Lee T. Schaller、Mark H. Norman

  DOI：10.1016/s0968-0896(98)00041-8

  日期：1998.6

  Analogues of 2-amino-N-(4-(4-(1, 2-benzisothiazol-3 -yl)-1-piperazinyl)-butyl)benzamide hydrochloride (1192U90) were prepared and evaluated in receptor binding assays for the dopamine D-2, serotonin 5-HT1a, and serotonin 5-HT2 receptors. Eight compounds have been synthesized in which the amide group of 1192U90 has been replaced with a variety of functional groups (i.e, ester, ketone, thioamide, butyramide, butyranilide, sulfonamide, alkoxyamide and hydrazide). These compounds exhibited moderate to potent affinities (0.55-200 nM) for all three receptors. Several analogues exhibited improved selectivity for the 5-HT2 receptor with D-2/5-HT2 binding ratios greater than 1192U90. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Inhibitory effect of novel S,N-bisphosphonates on some carcinoma cell lines, osteoarthritis, and chronic inflammation
  作者：Azza A. Kamel、Athina Geronikaki、Wafaa M. Abdou

  DOI：10.1016/j.ejmech.2012.02.047

  日期：2012.5

  A new series of S,N-bisphosphonate derivatives was synthesized and evaluated as antitumor agents against breast-, cervix-, liver, and colon cancer diseases. Antiarthritic and antichronic inflammatory properties of the new bisphosphonates (BPs) were also investigated. The studies demonstrated an efficient site selective method for making condensation products of BP-derivatives in high yields from thiazinethiones and tetraethyl methylenebisphosphonate reagent. The bioscreening evaluation showed that one of the tested BPs exhibited remarkable antitumor activity against the four tested carcinoma cell lines; nevertheless, all tested S,N-BP-derivatives (11 compounds) showed significant to moderate anti-inflammatory activity and capable of inhibiting polyarthritis. (C) 2012 Elsevier Masson SAS. All rights reserved.