2-(1-azidoethyl)benzo[d]oxazole | 1169393-53-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-(1-azidoethyl)benzo[d]oxazole
• 英文别名: 2-(1-Azidoethyl)-1,3-benzoxazole；2-(1-azidoethyl)-1,3-benzoxazole
• CAS: 1169393-53-6
• 化学式: C₉H₈N₄O
• 分子量: 188.189
• InChiKey: FGGAVMZMKNZWPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-azidoethyl)benzo[d]oxazole 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以74%的产率得到1-(苯并[d]恶唑-2-基)乙胺
  参考文献：
  名称：

  脂肪酶催化动力学拆分立体选择性化学酶法合成对映体纯 1-（杂芳基）乙胺

  摘要：

  1-（杂芳基）乙胺家族的有效化学合成和酶动力学拆分已使用脂肪酶进行，脂肪酶负责制备高光学纯度的含氮化合物。因此，Candida antarctica 脂肪酶 B 型已被确定为立体选择性生产相应对映体富集的 (R)-乙酰胺和 (S)-胺的极好生物催化剂。在反应性和对映选择性方面观察到环中杂原子的类似作用，反应一天后获得具有优异对映纯度的苯并恶唑、苯并噻唑和苯并咪唑衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900150
• 作为产物：
  描述：

  1-(苯并[d]恶唑-2-基)乙胺 在 copper(ll) sulfate pentahydrate 、 triflic azide 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 生成 2-(1-azidoethyl)benzo[d]oxazole
  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

文献信息

• Stereoselective Chemoenzymatic Synthesis of Enantiopure 1-(Heteroaryl)ethanamines by Lipase-Catalysed Kinetic Resolutions
  作者：Sergio Alatorre-Santamaría、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1002/ejoc.200900150

  日期：2009.5

  The efficient chemical synthesis and enzymatic kinetic resolution of a family of 1-(heteroaryl)ethanamines have been performed with lipases responsible for the preparation of nitrogenated compounds in high optical purity. Thus, Candida antarctica lipase type B has been identified as an excellent biocatalyst for the stereoselective production of the corresponding enantiomerically enriched (R)-acetamides

  1-（杂芳基）乙胺家族的有效化学合成和酶动力学拆分已使用脂肪酶进行，脂肪酶负责制备高光学纯度的含氮化合物。因此，Candida antarctica 脂肪酶 B 型已被确定为立体选择性生产相应对映体富集的 (R)-乙酰胺和 (S)-胺的极好生物催化剂。在反应性和对映选择性方面观察到环中杂原子的类似作用，反应一天后获得具有优异对映纯度的苯并恶唑、苯并噻唑和苯并咪唑衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• 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.