N-hexylbenzotriazole-1-carboxamide | 934701-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: N-hexylbenzotriazole-1-carboxamide
• CAS: 934701-88-9
• 化学式: C₁₃H₁₈N₄O
• 分子量: 246.312
• InChiKey: CWNPCDDKESBHOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1H-1,2,3-苯并三唑-1-基(正己基)甲酮 在 sodium azide 、 iron(III) chloride hexahydrate 、 T406石油添加剂 作用下， 以 水 、 丙酮 为溶剂， 反应 3.08h， 以71.7%的产率得到N-hexylbenzotriazole-1-carboxamide
  参考文献：
  名称：

  用苯并三唑原位捕获异氰酸酯 - 通过 Curtius 重排制备氨基甲酰基苯并三唑作为异氰酸酯替代品

  摘要：

  N-芳基和N-烯基氨基甲酰基苯并三唑通过Curtius重排从酰基叠氮化物和苯并三唑以良好到优异的产率制备，而N-烷基氨基甲酰基苯并三唑由N-烷酰基苯并三唑和叠氮化钠在一锅中形成。氨基甲酰基苯并三唑可用作稳定的异氰酸酯替代物，正如其与胺反应以优异的产率合成脲所证明的那样。

  DOI：

  10.1055/s-0029-1217820

文献信息

• CARBAMOYLBENZOTRIAZOLE DERIVATIVES AS INHIBITORS OF LIPASES AND PHOSPHOLIPASES
  申请人：Petry Stefan

  公开号：US20080287503A1

  公开（公告）日：2008-11-20

  The invention relates to carbamoylbenzotriazole derivatives of general formula (I), which are defined as cited in the description, to their pharmaceutically applicable salts and to their use as medicaments.

  这项发明涉及一般式(I)的氨基甲酰基苯并三唑衍生物，其在描述中被定义，以及它们的药用盐和作为药物的用途。
• One-pot preparation of carbamoyl benzotriazoles and their applications in the preparation of ureas, hydrazinecarboxamides and carbamic esters
  作者：Hui Mao、Huili Liu、Yawei Tu、Zhiyun Zhong、Xin Lv、Xiaoxia Wang

  DOI：10.2298/jsc150126069m

  日期：——

  synthesized in one-pot from carboxylic acids, diphenylphosphorazidate (DPPA) and benzotriazole (BtH). The reactivity and applications of carbamoyl benzotriazoles were also explored. Carbamoyl benzotriazoles react smoothly with amino acids, hydrazines and alcohols respectively, thus providing facile access to the corresponding ureas, hydrazinecarboxamides and carbamic esters in good to excellent yields

  氨基甲酰基苯并三唑可方便地由羧酸，叠氮磷酸二苯酯（DPPA）和苯并三唑（BtH）一锅合成。还探讨了氨基甲酰基苯并三唑的反应性和应用。氨基甲酰基苯并三唑分别与氨基酸，肼和醇平稳反应，因此可以轻松获得相应的脲，肼甲酰胺和氨基甲酸酯，收率高至优异。
• Pharmacophore Identification and Scaffold Exploration to Discover Novel, Potent, and Chemically Stable Inhibitors of Acid Ceramidase in Melanoma Cells
  作者：Jose Antonio Ortega、Jose M. Arencibia、Giuseppina La Sala、Marco Borgogno、Inga Bauer、Luca Bono、Clarissa Braccia、Andrea Armirotti、Stefania Girotto、Anand Ganesan、Marco De Vivo

  DOI：10.1021/acs.jmedchem.7b00472

  日期：2017.7.13

  Acid ceramidase (AC) hydrolyzes ceramides, which are central lipid messengers for metabolism and signaling of sphingolipids. A growing body of evidence links deregulation of sphingolipids to several diseases, including cancer. Indeed, AC expression is abnormally high in melanoma cells. AC inhibition may thus be key to treating malignant melanoma. Here, we have used a systematic scaffold exploration to design a general pharmacophore for AC inhibition. This pharmacophore comprises a 6 + 5 fused ring heterocycle linked to an aliphatic substituent via a urea moiety. We have thus identified the novel benzimidazole derivatives 10, 21, 27, and 30, which are highly potent AC inhibitors. Their chemical and metabolic stabilities are comparable or superior to those of previously reported AC inhibitors. Moreover, they are potent against endogenous AC in intact melanoma cells. These novel inhibitors merit further characterization and can serve as a promising starting point for the discovery of new antimelanoma therapeutics.
• CARBAMOYLBENZOTRIAZOL-DERIVATE ALS INHIBITOREN VON LIPASEN UND PHOSPHOLIPASEN
  申请人：SANOFI

  公开号：EP1940807B1

  公开（公告）日：2015-06-17
• US7897625B2
  申请人：——

  公开号：US7897625B2

  公开（公告）日：2011-03-01