2-(4'-氨基-3'-氯苯基)苯并噻唑 | 178804-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-(4'-氨基-3'-氯苯基)苯并噻唑
• 英文名称: 4-benzothiazol-2-yl-2-chlorophenylamine
• 英文别名: 2-(4'-amino-3'-chlorophenyl)benzothiazole；4-(2-Benzothiazolyl)-2-chloro-benzenamine；4-(1,3-benzothiazol-2-yl)-2-chloroaniline
• CAS: 178804-10-9
• 化学式: C₁₃H₉ClN₂S
• mdl: MFCD00950807
• 分子量: 260.747
• InChiKey: VMHNOJKXMWYAGM-UHFFFAOYSA-N

物化性质

• 沸点：
  440.1±55.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4'-氨基-3'-氯苯基)苯并噻唑 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 N-(4-(benzo[d]thiazol-2-yl)-2-chlorophenyl)-2-phenoxyacetamide
  参考文献：
  名称：

  Synthesis of some N-[4-(benzothiazole-2yl) phenyl]-2-aryloxyacetamide derivatives and their anticancer activities

  摘要：

  In this study, some N-[4-(Benzothiazole-2-yl)phenyl]-2-aryloxyacetamide derivatives were prepared by reacting N-[4-(benzothiazole-2yl)phenyl]-2-chloroacetamide and different substituent phenol or thiophenol derivatives. The anticancer activities of the compounds obtained were investigated. It was observed that some of the compounds, namely 25 and 38, showed notable anticancer activity.

  DOI：

  10.3109/14756366.2011.599030
• 作为产物：
  描述：

  4-(2-苯并噻唑基)苯胺 在 一氯化碘 、 溶剂黄146 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4'-氨基-3'-氯苯基)苯并噻唑
  参考文献：
  名称：

  Antitumor Benzothiazoles. 7. Synthesis of 2-(4-Acylaminophenyl)benzothiazoles and Investigations into the Role of Acetylation in the Antitumor Activities of the Parent Amines

  摘要：

  2-(4-Aminophenyl)benzothiazoles display potent and selective antitumor activity against inter alia breast, ovarian, colon, and renal cell lines, but their mechanism of action, though yet to be defined, may be novel. Metabolism is suspected to play a central role in the mode of action of these benzothiazoles since drug uptake and biotransformation were observed in sensitive cell lines (e.g., breast MCF-7 and MDA 468 cells) in vitro, whereas insensitive cell lines (e.g., prostate PC 3 cells) showed negligible uptake and biotransformation. N-Acyl derivatives of the arylamines have been synthesized, and in vitro studies confirm N-acetylation and oxidation as the main metabolic transformations of 2-(4-aminophenyl)benzothiazoles, with the predominant process being dictated by the nature of the 3'-substituent. The prototype amine 3 underwent mainly N-acetylation in vitro, while 3'-substituted analogues 4 and 5 were primarily oxidized. N-Acetylation of 4 to 11 exerts a drastic dyschemotherapeutic effect in vitro, but acetylation of the halogeno congeners 5-7 gave acetylamines 12-14 which substantially retain selective antitumor activity. In vivo pharmacokinetic studies in rats confirmed rapid and exclusive N-acetylation of the 3'-methyl analogue 4, but less acetylation with the 3'-chloro analogue 5. Distinct expression patterns of N-acetyltransferase NAT1 and NAT2 have been demonstrated in our panel of cell lines.

  DOI：

  10.1021/jm981076x

文献信息

• Synthesis of 2-(4-aminophenyl)benzothiazoles using MF resin supported H+ under solvent free conditions
  作者：Yingjie Lei、Xinshi Wu、Guochun Zhang、Cuiling Ai

  DOI：10.1134/s1070363215030251

  日期：2015.3

  A simple and convenient approach to 2-(4-aminophenyl)benzothiazole derivatives by condensation of o-aminothiophenol with (un)substituted p-aminobenzoic acid under the action of melamine formaldehyde resin (MFR) supported sulfuric acid under microwave irradiation (MW) and solvent-free conditions has been developed. Structures of the corresponding products were elucidated by IR, 1H NMR spectra, and elemental

  在三聚氰胺甲醛树脂（MFR）负载的硫酸作用下，邻位氨基硫酚与（未）取代的对氨基苯甲酸缩合，在微波辐射（MW）下，生成2-（4-氨基苯基）苯并噻唑衍生物的简便方法。已经开发出无溶剂条件。通过IR，1 H NMR光谱和元素分析来阐明相应产物的结构。该树脂可以容易地回收并再用于后续反应。
• 2-arylbenzazole compounds
  申请人：Cancer Research Campaign Technology Limited

  公开号：US06034246A1

  公开（公告）日：2000-03-07

  There are disclosed herein 2-phenylbenzazole compounds having a 3'-substituent and a 4'-NR.sup.2 R.sup.6 substituent in the phenyl group where R.sup.5 and R.sup.6 are each hydrogen or alkyl, or where the $'-NR.sup.5 R.sup.6 substituent is N-acyl (or N-benzoyl). There are also disclosed 2-phenylbenzazole compounds in the form of 4'-N sulphamate salts. Such compounds exhibit significant selective cytotoxic activity in respect of tumor cells and provide potentially useful chemotherapeutic agents for selective treatment of a range of cancers.

  本文披露了含有3'-取代基和4'-NR.sup.2 R.sup.6取代基的2-苯基苯并咪唑化合物，其中苯基中的R.sup.5和R.sup.6分别为氢或烷基，或者4'-NR.sup.5 R.sup.6取代基为N-酰基（或N-苯甲酰基）。还披露了以4'-N磺酸盐形式存在的2-苯基苯并咪唑化合物。这些化合物在肿瘤细胞中表现出显著的选择性细胞毒活性，并为选择性治疗多种癌症提供了潜在有用的化疗药物。
• [EN] SUBSTITUTED 2-ARYLBENZAZOLE COMPOUNDS AND THEIR USE AS ANTITUMOUR AGENTS<br/>[FR] COMPOSES DE 2-ARYLBENZAZOLE SUBSTITUES ET LEUR UTILISATION COMME AGENTS ANTITUMORAUX
  申请人：CANCER RES CAMPAIGN TECH

  公开号：WO2001014354A1

  公开（公告）日：2001-03-01

  Substituted 2-phenylbenzazole compounds of formula (I) wherein X represents S or O and Q represents a direct bond, -CH2- or -CH=CH-, exhibit selective antiproliferative activity in respect of mammalian tumour cells. At least in preferred embodiments the benzene ring of the benzazole nucleus has a halogen substituent, preferably fluorine, and the 2-phenyl group has a 4'-amino substituent which may be conjugated with an amino acid to provide a water soluble amino acid amide prodrug or salt thereof.

  公式（I）中的2-苯基苯并咪唑化合物，其中X代表S或O，Q代表直接键，-CH2-或-CH=CH-，在哺乳动物肿瘤细胞中表现出选择性抗增殖活性。在至少优选实施例中，苯并咪唑核的苯环具有卤素取代基，优选为氟，而2-苯基基团具有4'-氨基取代基，可以与氨基酸结合以提供水溶性氨基酸酰胺前药或其盐。
• Substituted 2-arylbenzazole compounds and their use as antitumour agents
  申请人：Stevens Malcolm F. G.

  公开号：US06858633B1

  公开（公告）日：2005-02-22

  Substituted 2-phenylbenzazole compounds of formula (I) wherein X represents S or O and Q represents a direct bond, —CH2— or —CH═Ch—, exhibt selective antiproliferactive activity in respect of mammalian tumour cells. At least in preferred enbodiments the benzene ring of the benzazole nucleus has a halogen substituent, preferably flourine, and the 2-phenyl group has a 4′-amino substituent which may be conjugated with an amino acid to provide a water soluble amino acid amide prodrug or salt thereof.

  公式(I)中的2-苯基苯并咪唑化合物，其中X代表S或O，Q代表直接键，-CH2-或-CH═CH-，在哺乳动物肿瘤细胞方面表现出选择性抗增殖活性。至少在优选实施例中，苯并咪唑核的苯环具有卤素取代基，优选为氟，而2-苯基基团具有4'-氨基取代基，可以与氨基酸共轭以提供水溶性氨基酸酰胺前药或其盐。
• Antitumor Benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines <i>in </i><i>Vitro </i>and <i>in Vivo</i>
  作者：Dong-Fang Shi、Tracey D. Bradshaw、Samantha Wrigley、Carol J. McCall、Peter Lelieveld、Iduna Fichtner、Malcolm F. G. Stevens

  DOI：10.1021/jm9600959

  日期：1996.1.1

  A new series of 2-(4-aminophenyl)benzothiazoles substituted in the phenyl ring and benzothiazole moiety has been synthesized by simple, high-yielding routes. The parent molecule 5a shows potent inhibitory activity in vitro in the nanomolar range against a panel of human breast cancer cell lines, but is inactive (IC50 > 30 mu M) against other cell types: activity against the sensitive breast lines MCF-7 and MDA 468 is characterized by a biphasic dose-response relationship. Structure-activity relationships derived using these cell types has revealed that activity follows the heterocyclic sequence benzothiazole > benzoxazole much greater than benzimidazole and that 2-(4-aminophenyl)benzothiazoles bearing a 3'-methyl- 9a, 3'-bromo- 9c, 3'- iodo- 9f, and 3'-chloro-substituent 9i are especially potent and their activity extends to ovarian, lung, and renal cell lines. Four compounds have been evaluated in vivo against human mammary carcinoma models in nude mice. Compound 9a showed the most potent growth inhibition against the ER(+) (MCF-7 and BO) and ER(-) (MT-1 and MT-3) tumors. Our efforts to identify a pharmacological mechanism of action for these intriguing compounds have not, as yet, been successful.