N²,N²-diethyl-benzothiazole-2,6-diamine | 329024-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N²,N²-diethyl-benzothiazole-2,6-diamine
• 英文别名: N²,N²-diethyl-benzothiazole-2,6-diyldiamine；N²,N²-Diaethyl-benzothiazol-2,6-diyldiamin；2-Diaethylamino-6-amino-benzothiazol；2-N,2-N-diethyl-1,3-benzothiazole-2,6-diamine
• CAS: 329024-82-0
• 化学式: C₁₁H₁₅N₃S
• mdl: MFCD18262641
• 分子量: 221.326
• InChiKey: HVXHTESIDDYCQN-UHFFFAOYSA-N

物化性质

• 沸点：
  363.0±34.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N²,N²-diethyl-benzothiazole-2,6-diamine 在 4-二甲氨基吡啶 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 15.0h， 生成 3-chloro-N-(3-cyano-4-((2-(diethylamino)benzo[d]thiazol-6-yl)amino)-6-methylquinolin-7-yl)propanamide
  参考文献：
  名称：

  Design, synthesis and antitumor activity of 6,7-disubstituted-4-(heteroarylamino)quinoline-3-carbonitrile derivatives

  摘要：

  A series of new 6,7-disubstituted-4-(benzothiazol-6-ylamino)quinoline-3-carbonitrile derivatives (12a-I) were synthesized. The cytotoxicity of 12 new compounds was evaluated in AGS, HepG2 and HT-29 cell lines The results showed that compounds 12g, 12h, 12i, 12k and 121 displayed more potent cytotoxic activities than Bosutinib, compound 121 exhibited the most potent antitumor activity among the tested compounds. (C) 2010 Qi Dong You Published by Elsevier B V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.01.016
• 作为产物：
  描述：

  N,N-diethyl-6-nitrobenzo[d]thiazol-2-amine 在 palladium on activated charcoal 氢气 作用下， 生成 N²,N²-diethyl-benzothiazole-2,6-diamine
  参考文献：
  名称：

  带有位置2取代基的6-硝基-和6-氨基-苯并噻唑及其相应的邻氨基苯甲酸衍生物对婴儿利什曼原虫和阴道毛滴虫的体外活性。

  摘要：

  研究了在位置2带有不同链的6-硝基和6-氨基-苯并噻唑及其相应的邻氨基苯甲酸衍生物在体外对婴儿利什曼原虫和阴道毛滴虫的寄生虫的抗寄生虫特性，以及它们对人单核细胞的毒性。生物学研究确定，抗原生动物特性很大程度上取决于位置2取代基团的化学结构。化合物C1，2-[（（2-氯-苯并噻唑-6-基）氨基]苯甲酸，对阴道锥虫物种的寄生虫表现出有趣的抗增殖活性，而化合物C11，2-（[2-[（2-羟乙基）氨基]-苯并噻唑-6-基]氨基）苯甲酸，以其胞内a节肢动物形式表现出对婴儿乳杆菌的寄生虫有希望的活性。

  DOI：

  10.1128/aac.46.8.2588-2594.2002

文献信息

• Reactivity of 2-Aminothiazole and 2- or 6-Aminobenzothiazole Derivatives Towards the Triphenylbismuth Diacetate/Catalytic Copper Diacetate Phenylation System
  作者：Abdellah Miloudi、Douniazad El-Abed、Gérard Boyer、Jean Pierre Finet、Jean Pierre Galy、Didier Siri

  DOI：10.1002/ejoc.200300656

  日期：2004.4

  The copper diacetate catalysed reaction of triphenylbismuth diacetate with 6-aminobenzothiazole compounds afforded selectively the 6-phenylamino derivatives in good to high yields. A similar reaction with 2-aminothiazole or 2-aminobenzothiazole compounds gave mixtures of the monophenylated and diphenylated products 2-phenylaminothiazole and 2-(N-phenylamino)-3-N′-phenylthiazole derivatives, respectively

  二乙酸铜催化的二乙酸三苯基铋与 6-氨基苯并噻唑化合物的反应选择性地以良好到高产率提供了 6-苯基氨基衍生物。与 2-氨基噻唑或 2-氨基苯并噻唑化合物的类似反应分别得到单苯基化和二苯基化产物 2-苯基氨基噻唑和 2-(N-苯基氨基)-3-N'-苯基噻唑衍生物的混合物，其中二苯基产物占优势。使用 SAM1/D 和 CHAIN 方法对 2-氨基苯并噻唑 - 铜 (III) 中间体的演化进行的半经验计算与实验结果具有良好的定性一致性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Takahashi et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 41,43
  作者：Takahashi et al.

  DOI：——

  日期：——
• DNA-damaging activity and mutagenicity of 16 newly synthesized thiazolo[5,4-a]acridine derivatives with high photo-inducible cytotoxicity
  作者：Carole Di Giorgio、Anna Nikoyan、Laetitia Decome、Céline Botta、Maxime Robin、Jean-Pierre Reboul、Anne-Sophie Sabatier、Alain Matta、Michel De Méo

  DOI：10.1016/j.mrgentox.2007.10.022

  日期：2008.2

  The discovery of the potent anticancer properties of natural alkaloids in the pyrido-thiazolo-acridine series has suggested that thiazolo-acridine derivatives could be of great interest. In a continuous attempt to develop DNA-binding molecules and DNA photo-cleavers, 16 new thiazolo[5,4a]acridines were synthesized and studied for their photo-inducible DNA-intercalative, cytotoxic and mutagenic activities, by use of the DNA methyl-green bioassay, the Alamar Blue (R) viability assay and the Salmonella mutagenicity test using strains TA97a and TA98 with and without metabolic activation and photo-activation. Without photo-activation, one compound showed a DNA-intercalative activity in the DNA major groove while three compounds displayed intercalating properties after photo-activation. In the dark, four molecules possessed cytotoxic activities against a THP 1 acute monocytic leukemia cell line while 15 derivatives displayed photo-inducible cytotoxic activity against this cell line. All compounds were mutagenic in strain TA97a with metabolic activation (+S9mix) and 15 molecules were mutagenic in strain TA98 without activation (-S9mix). Study of the quantitative structure-activity relationships (QSAR) from the Salmonella mutagenicity data revealed that several descriptors could describe cytotoxic and mutagenic activities after photo-activation. From the results of the mutagenicity test, four compounds with elevated mutagenic activities were selected for additional experiments. Their, capacities to induce single-strand breaks (SSB) and chromosome-damaging effects were monitored by the comet and the micronucleus assays in normal human keratinocytes. Comparison of the minimal genotoxic concentrations showed that two compounds possessed higher capacities to induce SSB after photo-activation. In the micronucleus assay, three molecules were able to induce high numbers of micronuclei following photo-activation. Overall, the results of this study confirm that acridines are predominantly genotoxic via a DNA-intercalating mechanism in the dark, while DNA-adducts were probably induced following photo-activation. (C) 2007 Elsevier B.V. All rights reserved.
• Nishizawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1943, vol. 63, p. 140,142
  作者：Nishizawa

  DOI：——

  日期：——