2-(4-amino-3-iodophenyl)-5-fluorobenzothiazole | 328087-22-5

• 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: 2-(4-amino-3-iodophenyl)-5-fluorobenzothiazole
• 英文别名: 5-fluoro-2-(4'-amino-3'-iodophenyl)benzothiazole；4-(5-fluoro-1,3-benzothiazol-2-yl)-2-iodoaniline
• CAS: 328087-22-5
• 化学式: C₁₃H₈FIN₂S
• 分子量: 370.189
• InChiKey: IMJKFJZKKOFDFI-UHFFFAOYSA-N

物化性质

• 熔点：
  187-188 °C
• 沸点：
  478.0±55.0 °C(Predicted)
• 密度：
  1.849±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 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：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-amino-3-iodophenyl)-5-fluorobenzothiazole 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 34.0h， 生成 2-Ethynyl-4-(5-fluoro-benzothiazol-2-yl)-phenylamine
  参考文献：
  名称：

  Antitumour benzothiazoles. Part 20: 3′-Cyano and 3′-Alkynyl-Substituted 2-(4′-Aminophenyl)benzothiazoles as new potent and selective analogues

  摘要：

  The synthesis of a new series of antitumour 2-(4-aminophenyl)benzothiazole analogues, substituted in the 3'-position by cyano or alkynyl groups, is described. Several of the analogues, notably the 5-fluorinated compounds 7c and 9c, were found to possess potent in vitro activity against MCF-7 and MDA 468 human cancer cell lines. More comprehensive in vitro analysis (NCI 60-cell line) established compound 7c as a particularly potent and selective 2-(4-aminophenyl)benzothiazole analogue. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00930-7
• 作为产物：
  描述：

  2-(4-aminophenyl)-5-fluorobenzothiazole 在 一氯化碘 、 溶剂黄146 作用下， 反应 2.0h， 以63%的产率得到2-(4-amino-3-iodophenyl)-5-fluorobenzothiazole
  参考文献：
  名称：

  Antitumor Benzothiazoles. 14. Synthesis and in Vitro Biological Properties of Fluorinated 2-(4-Aminophenyl)benzothiazoles

  摘要：

  Synthetic routes to a series of mono- and difluorinated 2-(4-amino-3-substituted-phenyl)benzothiazoles have been devised. Whereas mixtures of regioisomeric 5- and 7-fluorobenzothiazoles were formed from the established Jacobsen cyclization of precursor 3-fluorothiobenzanilides, two modifications to this general process have allowed the synthesis of pure samples of these target compounds. Fluorinated 2-(4-aminophenyl)benzothiazoles were potently cytotoxic (GI(50) < 1 nM) in vitro in sensitive human breast MCF-7 (ER+) and MDA 468 (ER-) cell lines but inactive (GI(50) > 10 muM) against PC 3 prostate, nonmalignant HBL 100 breast, and HCT 116 colon cells. The biphasic dose-response relationship characteristically shown by the benzothiazole series against sensitive cell lines was exhibited by the 4- and 6-fluorobenzothiazoles (10b,d) but not by the 5- and 7-fluoro-benzothiazoles (10h,i). The most potent broad spectrum agent in the NCI cell panel was 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (10h) which, unlike the g-fluoro isomer (10d), produces no exportable metabolites in the presence of sensitive MCF-7 cells. Induction of cytochrome P450 CYP1A1, a crucial event in determining the antitumor specificity of this series of benzothiazoles, was not compromised. 10h is currently the focus of pharmaceutical and preclinical development.

  DOI：

  10.1021/jm001104n

文献信息

• 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X代表S或O，Q代表直接键，—CH2—或—CH═CH—的2-苯基苯并唑化合物表现出对哺乳动物肿瘤细胞的选择性抗增殖活性。在至少首选实施例中，苯并唑核的苯环具有卤素取代基，优选是氟，并且2-苯基团具有4'-氨基取代基，可能与氨基酸共轭以提供水溶性氨基酸酰胺前药或其盐。
• [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。
• [EN] USE OF 4-(BENZOTHIAZOLE-2-YL)ARYLAMINE COMPOUND IN TREATING STOMACH CANCER<br/>[FR] UTILISATION D'UN COMPOSÉ DE 4-(BENZOTHIAZOLE-2-YL)ARYLAMINE DANS LE TRAITEMENT DU CANCER DE L'ESTOMAC<br/>[ZH] 4-(苯并噻唑-2-基)芳胺类化合物治疗胃癌的用途
  申请人：UNIV NOTTINGHAM

  公开号：WO2020098516A1

  公开（公告）日：2020-05-22

  本发明公开了一类4-(苯并噻唑-2-基)芳胺类化合物治疗胃癌的用途，其为通式(I)所示的化合物或其药学上可接受的盐。
• Metabolically Stabilized Benzothiazoles for Imaging of Amyloid Plaques
  作者：Gjermund Henriksen、Andrea I. Hauser、Andrew D. Westwell、Behrooz H. Yousefi、Markus Schwaiger、Alexander Drzezga、Hans-Jürgen Wester

  DOI：10.1021/jm061466g

  日期：2007.3.1

  Six new N-C-11-labeled aminophenylbenzothiazoles substituted with fluorine in different positions have been synthesized and evaluated as amyloid-beta binding ligands. Our structure-property relationship studies show that the substitution pattern of the phenyl ring and the benzothiazole moiety has an influence on the metabolic stability, which in turn has an effect on the brain uptake kinetics. Two lead compounds have been identified with improved physicochemical characteristics for A beta-plaque imaging in vivo.
• SUBSTITUTED 2-ARYLBENZAZOLE COMPOUNDS AND THEIR USE AS ANTITUMOUR AGENTS
  申请人：Cancer Research Ventures Limited

  公开号：EP1204650B1

  公开（公告）日：2006-04-19