(2R)-2-isothiocyanatooctane | 737761-97-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 英文名称: (2R)-2-isothiocyanatooctane
• CAS: 737761-97-6
• 化学式: C₉H₁₇NS
• 分子量: 171.307
• InChiKey: RXAAZXUXIQEORL-SECBINFHSA-N

物化性质

• 沸点：
  245.3±9.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氯-4-氟苯胺 、 (2R)-2-isothiocyanatooctane 以 甲醇 为溶剂， 反应 1.0h， 以74%的产率得到1-(3-chloro-4-fluorophenyl)-3-((R)-octan-2-yl)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)-2-氨基辛烷 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2R)-2-isothiocyanatooctane
  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

• 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.