(S)-{1-[4-(6-fluoro-benzothiazol-2-yl)-2-methylphenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-{1-[4-(6-fluoro-benzothiazol-2-yl)-2-methylphenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-[4-(6-fluoro-1,3-benzothiazol-2-yl)-2-methylanilino]-1-oxopropan-2-yl]carbamate
• 化学式: C₂₂H₂₄FN₃O₃S
• 分子量: 429.515
• InChiKey: VDGPATXYWRXGCQ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-{1-[4-(6-fluoro-benzothiazol-2-yl)-2-methylphenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到(S)-2-amino-N-[4-(6-fluoro-benzothiazol-2-yl)-2-methylphenyl]-propionamide hydrochloride
  参考文献：
  名称：

  Antitumor Benzothiazoles. 16. Synthesis and Pharmaceutical Properties of Antitumor 2-(4-Aminophenyl)benzothiazole Amino Acid Prodrugs

  摘要：

  A series of water-soluble L-lysyl- and L-alanyl-amide prodrugs of the lipophilic antitumor 2-(4-aminophenyl)benzothiazoles has been synthesized to address formulation and bioavailability issues related to the desired parenteral administration of the chosen clinical candidate. The prodrugs exhibit the required pharmaceutical properties of good water solubility (in weak acid) and stability at ambient temperature and degradation to free base in vivo. The lysyl-amide of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (NSC 710305, 6d) has been selected for phase 1 clinical evaluation.

  DOI：

  10.1021/jm011025r
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 、 2-(4-amino-3-methylphenyl)-6-fluorobenzothiazole 在 WSC*HCl 、 1-羟基苯并三唑 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以79%的产率得到(S)-{1-[4-(6-fluoro-benzothiazol-2-yl)-2-methylphenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Antitumor Benzothiazoles. 16. Synthesis and Pharmaceutical Properties of Antitumor 2-(4-Aminophenyl)benzothiazole Amino Acid Prodrugs

  摘要：

  A series of water-soluble L-lysyl- and L-alanyl-amide prodrugs of the lipophilic antitumor 2-(4-aminophenyl)benzothiazoles has been synthesized to address formulation and bioavailability issues related to the desired parenteral administration of the chosen clinical candidate. The prodrugs exhibit the required pharmaceutical properties of good water solubility (in weak acid) and stability at ambient temperature and degradation to free base in vivo. The lysyl-amide of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (NSC 710305, 6d) has been selected for phase 1 clinical evaluation.

  DOI：

  10.1021/jm011025r

文献信息

• Antitumor Benzothiazoles. 16. Synthesis and Pharmaceutical Properties of Antitumor 2-(4-Aminophenyl)benzothiazole Amino Acid Prodrugs
  作者：Ian Hutchinson、Sharon A. Jennings、B. Rao Vishnuvajjala、Andrew D. Westwell、Malcolm F. G. Stevens

  DOI：10.1021/jm011025r

  日期：2002.1.1

  A series of water-soluble L-lysyl- and L-alanyl-amide prodrugs of the lipophilic antitumor 2-(4-aminophenyl)benzothiazoles has been synthesized to address formulation and bioavailability issues related to the desired parenteral administration of the chosen clinical candidate. The prodrugs exhibit the required pharmaceutical properties of good water solubility (in weak acid) and stability at ambient temperature and degradation to free base in vivo. The lysyl-amide of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (NSC 710305, 6d) has been selected for phase 1 clinical evaluation.