tert-butyl [1-(1,3-benzothiazol-2-yl)-2-methylpropyl]carbamate | 1370749-12-4

• 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: tert-butyl [1-(1,3-benzothiazol-2-yl)-2-methylpropyl]carbamate
• 英文别名: tert-butyl N-[1-(benzo[d]thiazol-2-yl)-2-methylpropyl]carbamate；t-Butyl [1-(1,3-benzothiazol-2-yl)-2-methylpropyl]carbamate；tert-butyl N-[1-(1,3-benzothiazol-2-yl)-2-methylpropyl]carbamate
• CAS: 1370749-12-4
• 化学式: C₁₆H₂₂N₂O₂S
• 分子量: 306.429
• InChiKey: XQQGMYPXXCMVDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl [1-(1,3-benzothiazol-2-yl)-2-methylpropyl]carbamate 在 copper(ll) sulfate pentahydrate 、 triethylphosphite copper(I) iodide complex 、 三异丙基硅烷 、 triflic azide 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (E)-3-(1-(1-(benzo[d]thiazol-2-yl)-2-methylpropyl)-1H-1,2,3-triazol-4-yl)-N-hydroxyacrylamide
  参考文献：
  名称：

  Discovery and Extensive in Vitro Evaluations of NK-HDAC-1: A Chiral Histone Deacetylase Inhibitor as a Promising Lead

  摘要：

  Herein, further SAR studies of lead compound NSC746457 (Shen, J.; Woodward, R.; Kedenburg, J. P.; Liu, X. W.; Chen, M.; Fang, L. Y.; Sun; D. X.; Wang. P. G. J. Med. Chem. 2008, SI, 7417-7427) were performed, including the replacement of the trans-styryl moiety with a 2-substituted benzo-hetero aromatic ring and the introduction of a substituent onto the central methylene carbon. A promising chiral lead, S-(E)-3-(1-(1-(benzo[d]oxazol-2-yl)-2-methylpropyl)-1H-1,2,3-triazol-4-yl)-N-hydroxyacrylamide (12, NK-HDAC-1), was discovered and showed about 1 order of magnitude more potency than SAHA in both enzymatic and cellular assays. For the in vitro safety tests, NK-HDAC-1 was far less toxic to nontransformed cells than tumor cells and showed no significant inhibition activity against CYP-3A4. The pharmaceutical properties (LogD, solubility, liver micrsomal stability (t1/2), plasma stability (t1/2), and apparent permeability) strongly suggested that NK-HDAC-1 might be superior to SAHA in bioavailability and in vivo half-life.

  DOI：

  10.1021/jm201496g
• 作为产物：
  描述：

  N-Boc-DL-缬氨酸 在 TEA 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 tert-butyl [1-(1,3-benzothiazol-2-yl)-2-methylpropyl]carbamate
  参考文献：
  名称：

  新型吡嗪缀合物：合成、计算研究和针对 SARS-CoV-2 的抗病毒特性

  摘要：

  SARS-CoV-2 抗病毒药物开发：报告了吡嗪缀合物的设计和微波辅助合成。一些新合成的缀合物表现出比参比药物更好的抗病毒活性和选择性指标。所有先导化合物均表现出较低的细胞毒性。因此，这些缀合物可能导致 SARS-CoV-2 潜在候选药物的开发。

  DOI：

  10.1002/cmdc.202100476

文献信息

• A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids
  作者：M. Arfan、A. Tahira、A. Mannan、T. Fatima

  DOI：10.1134/s1070428020020190

  日期：2020.2

  -A simple trituration method for the synthesis of 2-substituted benzothiazoles derived from N-protected amino acids and 2-aminothiophenol using molecular iodine as a mild Lewis acid catalyst has been proposed. The reaction occurs in one step for 20-25 min in solve-free conditions and provides the target products in excellent yields.
• New Pyrazine Conjugates: Synthesis, Computational Studies, and Antiviral Properties against SARS‐CoV‐2
  作者：Israa A. Seliem、Adel S. Girgis、Yassmin Moatasim、Ahmed Kandeil、Ahmed Mostafa、Mohamed A. Ali、Mohamed S. Bekheit、Siva S. Panda

  DOI：10.1002/cmdc.202100476

  日期：2021.11.19

  Antiviral drug development for SARS-CoV-2: The design and microwave-assisted synthesis of pyrazine conjugates are reported. Some of the newly synthesized conjugates show better antiviral activity and selectivity indexes than those of the reference drug. All the lead compounds exhibited low cytotoxicity. Thus, these conjugates could lead to the development of potential drug candidates for SARS-CoV-2.

  SARS-CoV-2 抗病毒药物开发：报告了吡嗪缀合物的设计和微波辅助合成。一些新合成的缀合物表现出比参比药物更好的抗病毒活性和选择性指标。所有先导化合物均表现出较低的细胞毒性。因此，这些缀合物可能导致 SARS-CoV-2 潜在候选药物的开发。
• Discovery and Extensive <i>in Vitro</i> Evaluations of NK-HDAC-1: A Chiral Histone Deacetylase Inhibitor as a Promising Lead
  作者：Jingli Hou、Zhonghua Li、Qinghong Fang、Congran Feng、Hanwen Zhang、Weikang Guo、Huihui Wang、Guoxian Gu、Yinping Tian、Pi Liu、Ruihua Liu、Jianping Lin、Yi-kang Shi、Zheng Yin、Jie Shen、Peng George Wang

  DOI：10.1021/jm201496g

  日期：2012.4.12

  Herein, further SAR studies of lead compound NSC746457 (Shen, J.; Woodward, R.; Kedenburg, J. P.; Liu, X. W.; Chen, M.; Fang, L. Y.; Sun; D. X.; Wang. P. G. J. Med. Chem. 2008, SI, 7417-7427) were performed, including the replacement of the trans-styryl moiety with a 2-substituted benzo-hetero aromatic ring and the introduction of a substituent onto the central methylene carbon. A promising chiral lead, S-(E)-3-(1-(1-(benzo[d]oxazol-2-yl)-2-methylpropyl)-1H-1,2,3-triazol-4-yl)-N-hydroxyacrylamide (12, NK-HDAC-1), was discovered and showed about 1 order of magnitude more potency than SAHA in both enzymatic and cellular assays. For the in vitro safety tests, NK-HDAC-1 was far less toxic to nontransformed cells than tumor cells and showed no significant inhibition activity against CYP-3A4. The pharmaceutical properties (LogD, solubility, liver micrsomal stability (t1/2), plasma stability (t1/2), and apparent permeability) strongly suggested that NK-HDAC-1 might be superior to SAHA in bioavailability and in vivo half-life.