N-[(2-chloro-benzothiazol-6-yl)amino]benzoic acid | 138962-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(2-chloro-benzothiazol-6-yl)amino]benzoic acid
• 英文别名: N-(2-chloro-benzothiazol-6-yl)anthranilic acid；2-[(2-Chloro-1,3-benzothiazol-6-yl)amino]benzoic acid
• CAS: 138962-06-8
• 化学式: C₁₄H₉ClN₂O₂S
• 分子量: 304.757
• InChiKey: ZYVFSBUALPYACP-UHFFFAOYSA-N

物化性质

• 沸点：
  501.1±30.0 °C(Predicted)
• 密度：
  1.548±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(2-chloro-benzothiazol-6-yl)amino]benzoic acid 在 三氯氧磷 作用下， 反应 0.75h， 以92%的产率得到2,11-dichlorothiazolo[5,4-a]acridine
  参考文献：
  名称：

  Robin, Maxime; Faure, Robert; Perichaud, Alain, Heterocycles, 2000, vol. 53, # 2, p. 387 - 395

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-6-氨基苯并噻唑 、 2-溴苯甲酸 在 zinc/copper couple 、 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 3.0h， 以86%的产率得到N-[(2-chloro-benzothiazol-6-yl)amino]benzoic acid
  参考文献：
  名称：

  乌尔曼缩合的超声辐射：在制备二氧杂环戊二烯，二恶英，环戊和咪唑啉邻氨基苯甲酸衍生物中的应用

  摘要：

  报道了带有二氧杂环丁烷，二氧杂环丁烷，环戊和咪唑啉辅助环系统的N-芳基邻氨基苯甲酸衍生物的合成。与常规加热相比，N-芳基邻氨基苯甲酸的Ullmann-Goldberg缩合反应的收率和反应时间得到了改善。通过超声波照射。

  DOI：

  10.1002/jhet.5570390537

文献信息

• Ultrasonic irradiation of the ullmann condensation: Application to the preparation of dioxolo, dioxino, cyclopent, and imidazolo anthranilic acid derivatives
  作者：Maxime Robin、Valérie Pique、Robert Faure、Jean‐Pierre Galy

  DOI：10.1002/jhet.5570390537

  日期：2002.9

  The synthesis of N-aryl anthranilic acid derivatives bearing dioxolo, dioxino, cyclopent, and imidazolo supplementary ring systems is reported. The Ullmann-Goldberg condensation of the N-aryl anthranilic acid is improved in yield and reaction time, compared to conventional heating; by ultrasonic irradiation.

  报道了带有二氧杂环丁烷，二氧杂环丁烷，环戊和咪唑啉辅助环系统的N-芳基邻氨基苯甲酸衍生物的合成。与常规加热相比，N-芳基邻氨基苯甲酸的Ullmann-Goldberg缩合反应的收率和反应时间得到了改善。通过超声波照射。
• Thiazolo [5,4-α] acridines
  作者：Jacques Barbe、Gérard Boyer、Isabelle Carignano、José Elguero、Jean-Pierre Galy、Sandrine Morel、Razika Oughedani

  DOI：10.1016/s0040-4039(00)93582-2

  日期：1991.11

  The synthesis of thiazolo [5,4-a] acridines and acridin-9(10H)-ones by cyclisation of anthranilic acids is described. NMR (specially H-1 NMR) was used to ascertain their 'bent' structure.
• A Convenient Synthesis of N-Arylanthranilic Acids Using Ultrasonics in the Ullmann-Goldberg Condensation
  作者：Jean-Pierre Hanoun、Jean-Pierre Galy、Alphonse Tenaglia

  DOI：10.1080/00397919508015448

  日期：1995.8

  Ultrasonics efficiently promotes the Ullmann-Goldberg condensation of 2-halogenobenzoic acids and primary aromatic amines to obtain various N-arylanthranilic acids.
• Robin, Maxime; Faure, Robert; Perichaud, Alain, Heterocycles, 2000, vol. 53, # 2, p. 387 - 395
  作者：Robin, Maxime、Faure, Robert、Perichaud, Alain、Galy, Jean-Pierre

  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.