2-(4-aminophenyl)-5-fluorobenzothiazole | 328087-20-3

• 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-aminophenyl)-5-fluorobenzothiazole
• 英文别名: 4-(5-fluorobenzo[d]thiazol-2-yl)aniline；5-fluoro-2-(4'-amino-phenyl)benzothiazole；4-(5-Fluoro-benzothiazol-2-yl)-phenylamine；4-(5-fluoro-1,3-benzothiazol-2-yl)aniline
• CAS: 328087-20-3
• 化学式: C₁₃H₉FN₂S
• mdl: MFCD11636816
• 分子量: 244.292
• InChiKey: JRGMCDOYPGMMEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  bis-[2-(4'-nitrobenzanilide)-5-fluorophenyl] disulfide 在 盐酸 、 乙醇 、 tin(ll) chloride 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 16.0h， 生成 2-(4-aminophenyl)-5-fluorobenzothiazole
  参考文献：
  名称：

  Substituted 2-arylbenzazole compounds and their use as antitumour agents

  摘要：

  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。

  公开号：

  US06858633B1

文献信息

• 1-Phenyl-<i>N</i>-(benzothiazol-2-yl)methanimine derivatives as Middle East respiratory syndrome coronavirus inhibitors
  作者：Min-Qi Hu、Heng Li、Ying Lin、Ying Zhang、Jie Tang、Jian-Ping Zuo、Li-Fang Yu、Xian-Kun Tong、Wei Tang、Fan Yang

  DOI：10.1039/d0ra08442e

  日期：——

  A series of novel 1-phenyl-N-(benzothiazol-2-yl)methanimine derivatives were synthesized and their in vitro inhibitory potencies were evaluated on MERS-S pseudovirus.

  一系列新颖的1-苯基-N-(苯并噻唑-2-基)甲醛亚胺衍生物被合成，并在MERS-S假病毒上评估了它们的体外抑制效力。
• [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。
• COMPOUND FOR TREATING OR PREVENTING BREAST CANCER
  申请人：Jiangsu Atom Bioscience And Pharmaceutical Co., Ltd

  公开号：EP3296294A1

  公开（公告）日：2018-03-21

  Disclosed are a class of compounds for treating or preventing breast cancer, in particular 2-phenyl benzoselenazole compounds, and a pharmaceutically acceptable salt thereof and an easily hydrolysable prodrug thereof. Further disclosed are a pharmaceutical composition containing these compounds and the use of such compounds for for treating or preventing breast cancer in mammals. The compounds of the present invention can effectively inhibit or reduce the growth or proliferation of mammalian breast cancer cells, and at the same time, such compounds do not inhibit the growth of partial test cells, apart from breast cancer cells in mammals, and have a good selectivity. Such compounds show a more obvious medicinal effect, and have high selectivivity, low toxicity and few side effects.

  公开了一类用于治疗或预防乳腺癌的化合物，特别是 2-苯基苯并硒唑化合物，及其药学上可接受的盐和易水解的原药。进一步公开的是含有这些化合物的药物组合物，以及这些化合物用于治疗或预防哺乳动物乳腺癌的用途。本发明的化合物可以有效地抑制或减少哺乳动物乳腺癌细胞的生长或增殖，同时，除了哺乳动物的乳腺癌细胞外，这类化合物不会抑制部分试验细胞的生长，具有良好的选择性。这类化合物的药效更明显，选择性高，毒性低，副作用小。
• [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。
• Antitumor Benzothiazoles. 14. Synthesis and in Vitro Biological Properties of Fluorinated 2-(4-Aminophenyl)benzothiazoles
  作者：Ian Hutchinson、Mei-Sze Chua、Helen L. Browne、Valentina Trapani、Tracey D. Bradshaw、Andrew D. Westwell、Malcolm F. G. Stevens

  DOI：10.1021/jm001104n

  日期：2001.4.1

  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.