1-[(1R)-1-异硫氰酸基乙基]-4-甲氧基-苯 | 749261-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-[(1R)-1-异硫氰酸基乙基]-4-甲氧基-苯
• 中文别名: 乙酸,((1-(3-噻丁烷基)-1H-苯并咪唑-2-基)硫代)-,盐钾；(R)-(-)-1-(4-甲氧基苯基)乙基硫代异氰酸酯
• 英文名称: Benzene, 1-[(1R)-1-isothiocyanatoethyl]-4-methoxy-(9CI)
• 英文别名: 1-[(1R)-1-isothiocyanatoethyl]-4-methoxybenzene
• CAS: 749261-40-3
• 化学式: C₁₀H₁₁NOS
• 分子量: 193.269
• InChiKey: HOWJPQXDLZDTBF-MRVPVSSYSA-N

物化性质

• 沸点：
  298.1±23.0 °C(Predicted)
• 密度：
  1.122

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  53.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  8
• 危险品运输编号：
  UN 2922

反应信息

• 作为反应物：
  描述：

  3-氯-4-氟苯胺 、 1-[(1R)-1-异硫氰酸基乙基]-4-甲氧基-苯 以 甲醇 为溶剂， 反应 1.0h， 以68%的产率得到1-(3-chloro-4-fluorophenyl)-3-((R)-1-(4-methoxyphenyl)ethyl)thiourea
  参考文献：
  名称：

  Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: A novel class of anticancer agents

  摘要：

  A novel series of optically active 2-aminobenzothiazole derivatives were synthesized by reaction of optically active amine (1) with thiophosgene to obtain optically active isothiocyanates (IIa-h) which on condensation with 4-fluoro-3-chloro aniline (III) yielded various optically active thioureas (IVa-h). Further oxidative cyclisation in the presence of bromine and chloroform yielded title compounds (Va-h). The structures of these compounds were established by IR, H-1 NMR, C-13 NMR, Mass and HRMS. The compounds (IVA-h and Va-h) were evaluated for in vitro cytotoxicity against mouse Ehrlich Ascites Carcinoma (EAC) and two human cancer cell lines (MCF-7 and HeLa). In preliminary MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] cytotoxicity studies the optically active thiourea derivatives (IVe, IVf and IVh) were found most effective. In EAC cells the IC50 values for IVe, IVf, IVh and Vg were found in the range of 10-24 mu M, whereas in MCF-7 and HeLa cells the IC50 values were observed in the range of 15-30 mu M and 33-48 mu M, respectively. In alkaline comet assay the compounds (We and IVf) showed dose-dependent DNA damaging activity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.12.002
• 作为产物：
  描述：

  硫光气 、 (R)-(+)-1-(4-甲氧基苯)乙胺 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-[(1R)-1-异硫氰酸基乙基]-4-甲氧基-苯
  参考文献：
  名称：

  Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: A novel class of anticancer agents

  摘要：

  A novel series of optically active 2-aminobenzothiazole derivatives were synthesized by reaction of optically active amine (1) with thiophosgene to obtain optically active isothiocyanates (IIa-h) which on condensation with 4-fluoro-3-chloro aniline (III) yielded various optically active thioureas (IVa-h). Further oxidative cyclisation in the presence of bromine and chloroform yielded title compounds (Va-h). The structures of these compounds were established by IR, H-1 NMR, C-13 NMR, Mass and HRMS. The compounds (IVA-h and Va-h) were evaluated for in vitro cytotoxicity against mouse Ehrlich Ascites Carcinoma (EAC) and two human cancer cell lines (MCF-7 and HeLa). In preliminary MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] cytotoxicity studies the optically active thiourea derivatives (IVe, IVf and IVh) were found most effective. In EAC cells the IC50 values for IVe, IVf, IVh and Vg were found in the range of 10-24 mu M, whereas in MCF-7 and HeLa cells the IC50 values were observed in the range of 15-30 mu M and 33-48 mu M, respectively. In alkaline comet assay the compounds (We and IVf) showed dose-dependent DNA damaging activity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.12.002

文献信息

• [EN] NOVEL AMINOTHIAZOLE COMPOUNDS AND METHODS USING SAME<br/>[FR] NOUVEAUX COMPOSÉS AMINOTHIAZOLE ET LEURS MÉTHODES D'UTILISATION
  申请人：TEMPLE UNIVERSITY-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：WO2017015484A1

  公开（公告）日：2017-01-26

  The present invention includes novel aminothiazole compounds useful in preventing or treating cancer in a subject in need thereof. The present invention also includes methods of preventing or treating cancer in a subject in need thereof by administering to the subject a therapeutically effective amount of a compound of the invention.

  本发明涵盖了新型氨噻唑类化合物，可用于预防或治疗需要的患者的癌症。本发明还包括通过向患者投予本发明化合物的治疗有效量来预防或治疗需要的患者的癌症的方法。
• Aminothiazole compounds and methods using same
  申请人：Temple University—Of The Commonwealth System of Higher Education

  公开号：US10513516B2

  公开（公告）日：2019-12-24

  The present invention includes novel aminothiazole compounds of formula (I) useful in preventing or treating cancer in a subject in need thereof. The present invention also includes methods of preventing or treating cancer in a subject in need thereof by administering to the subject a therapeutically effective amount of a compound of the invention.

  本发明包括式 (I) 的新型氨基噻唑化合物 用于预防或治疗有需要的受试者的癌症。本发明还包括通过向有需要的受试者施用治疗有效量的本发明化合物来预防或治疗癌症的方法。
• NOVEL AMINOTHIAZOLE COMPOUNDS AND METHODS USING SAME
  申请人：Temple University Of The Commonwealth System Of Higher Education

  公开号：EP3324962A1

  公开（公告）日：2018-05-30
• Novel Aminothiazole Compounds and Methods Using Same
  申请人：Temple University-Of the Commonwealth System of Higher Education

  公开号：US20180215750A1

  公开（公告）日：2018-08-02

  The present invention includes novel aminothiazole compounds useful in preventing or treating cancer in a subject in need thereof. The present invention also includes methods of preventing or treating cancer in a subject in need thereof by administering to the subject a therapeutically effective amount of a compound of the invention.
• Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: A novel class of anticancer agents
  作者：S.N. Manjula、N. Malleshappa Noolvi、K. Vipan Parihar、S.A. Manohara Reddy、Vijay Ramani、Andanappa K. Gadad、Gurdial Singh、N. Gopalan Kutty、C. Mallikarjuna Rao

  DOI：10.1016/j.ejmech.2008.12.002

  日期：2009.7

  A novel series of optically active 2-aminobenzothiazole derivatives were synthesized by reaction of optically active amine (1) with thiophosgene to obtain optically active isothiocyanates (IIa-h) which on condensation with 4-fluoro-3-chloro aniline (III) yielded various optically active thioureas (IVa-h). Further oxidative cyclisation in the presence of bromine and chloroform yielded title compounds (Va-h). The structures of these compounds were established by IR, H-1 NMR, C-13 NMR, Mass and HRMS. The compounds (IVA-h and Va-h) were evaluated for in vitro cytotoxicity against mouse Ehrlich Ascites Carcinoma (EAC) and two human cancer cell lines (MCF-7 and HeLa). In preliminary MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] cytotoxicity studies the optically active thiourea derivatives (IVe, IVf and IVh) were found most effective. In EAC cells the IC50 values for IVe, IVf, IVh and Vg were found in the range of 10-24 mu M, whereas in MCF-7 and HeLa cells the IC50 values were observed in the range of 15-30 mu M and 33-48 mu M, respectively. In alkaline comet assay the compounds (We and IVf) showed dose-dependent DNA damaging activity. (C) 2008 Elsevier Masson SAS. All rights reserved.