N,N-diethyl-6-nitrobenzo[d]thiazol-2-amine | 3507-22-0

• 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: N,N-diethyl-6-nitrobenzo[d]thiazol-2-amine
• 英文别名: N,N-diethyl-6-nitro-1,3-benzothiazol-2-amine
• CAS: 3507-22-0
• 化学式: C₁₁H₁₃N₃O₂S
• 分子量: 251.309
• InChiKey: PXEHKSZBSSOSRN-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C
• 沸点：
  374.5±34.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-6-nitrobenzo[d]thiazol-2-amine 在 铁粉 、 溶剂黄146 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 12.0h， 生成 4-((2-(diethylamino)benzo[d]thiazol-6-yl)amino)-6-methyl-7-nitroquinoline-3-carbonitrile
  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：

  1,1-二乙基-3-(4-硝基苯基)硫脲 在 吡啶 、 碘苯二乙酸 、 nickel dibromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以62%的产率得到N,N-diethyl-6-nitrobenzo[d]thiazol-2-amine
  参考文献：
  名称：

  通过镍催化的分子内氧化CH官能团轻度合成2-取代的苯并噻唑。

  摘要：

  已经报道了从芳基硫脲开始制备2-氨基苯并噻唑的高效合成方法。通过使用镍催化剂，芳基硫脲进行分子内氧化CH键官能化，以良好至优异的产率得到所需的2-氨基苯并噻唑。该方案具有廉价的催化剂，催化剂用量低，反应条件温和，反应时间短，收率良好至优异的特点，并且可以轻松按比例放大至克级，而收率几乎没有下降。

  DOI：

  10.1021/acs.joc.9b02543

文献信息

• In Vitro Activities of Position 2 Substitution-Bearing 6-Nitro- and 6-Amino-Benzothiazoles and Their Corresponding Anthranilic Acid Derivatives against<i>Leishmania infantum</i>and<i>Trichomonas vaginalis</i>
  作者：Florence Delmas、Carole Di Giorgio、Maxime Robin、Nadine Azas、Monique Gasquet、Claire Detang、Muriel Costa、Pierre Timon-David、Jean-Pierre Galy

  DOI：10.1128/aac.46.8.2588-2594.2002

  日期：2002.8

  6-Nitro- and 6-amino-benzothiazoles bearing different chains in position 2 and their corresponding anthranilic acid derivatives were investigated for their in vitro antiparasitic properties against parasites of the species Leishmania infantum and Trichomonas vaginalis compared to their toxicity towards human monocytes. Biological investigations established that the antiprotozoal properties depended

  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。
• Copper(II)-Promoted Cascade Synthesis of 2-Aminobenzothiazoles Starting from 2-Iodoanilines and Sodium Dithiocarbamates
  作者：Hui Zhu、Shi-Bo Zhang、Xing Liu、Yu Cheng、Han-Ying Peng、Zhi-Bing Dong

  DOI：10.1002/ejoc.201801122

  日期：2018.11.8

  A facile and efficient formation of 2-aminobenzothiazoles by a copper(II)-promoted one-pot cascade process was developed. The desired 2-aminobenzothiazoles were synthesized in good to excellent yields (up to 97 %) in the presence of Cu(OAc)(2) and K2CO3, a variety of functional groups on 2-iodoanilines could be tolerated. The method features ligand-free and mild reaction conditions and good yields

  开发了通过铜 (II) 促进的一锅级联工艺轻松有效地形成 2-氨基苯并噻唑。在 Cu(OAc)(2) 和 K2CO3 存在下，所需的 2-氨基苯并噻唑以良好到优异的产率（高达 97%）合成，可以容忍 2-碘苯胺上的各种官能团。该方法具有无配体、反应条件温和、收率高等特点，说明了其在一些潜在生物活性化合物中的实际合成价值。
• 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：——