4-amino-N-isopentylbenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-N-isopentylbenzamide
• 英文别名: N-isopentyl-4-aminobenzamide；4-amino-N-(3-methylbutyl)benzamide
• 化学式: C₁₂H₁₈N₂O
• mdl: MFCD09807824
• 分子量: 206.288
• InChiKey: VAUAVJDYLXCRSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-amino-N-isopentylbenzamide 、 溴乙酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-(2-bromoacetylamino)-N-isoamylbenzamide
  参考文献：
  名称：

  Structure−Activity Relationships in the Binding of Chemically Derivatized CD4 to gp120 from Human Immunodeficiency Virus

  摘要：

  The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp 120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp 120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp 120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.

  DOI：

  10.1021/jm070564e
• 作为产物：
  描述：

  异戊胺 在 N-甲基吗啉 、 palladium on activated charcoal 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 反应 23.0h， 生成 4-amino-N-isopentylbenzamide
  参考文献：
  名称：

  NAMPT inhibitors

  摘要：

  揭示了抑制NAMPT活性的化合物，含有这些化合物的组合物以及治疗NAMPT表达期间的疾病的方法。

  公开号：

  US09187472B2

文献信息

• Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium‐Catalyzed Carbonylative Transformations
  作者：Chieh‐Hung Tien、Alina Trofimova、Aleksandra Holownia、Branden S. Kwak、Reed T. Larson、Andrei K. Yudin

  DOI：10.1002/anie.202010211

  日期：2021.2.19

  highlighted in the palladium‐catalyzed aminocarbonylation, alkoxycarbonylation, carbonylative Sonogashira coupling, and carbonylative Suzuki–Miyaura coupling of aryl halides. A variety of amides, esters, (hetero)aromatic ynones, and bis(hetero)aryl ketones were synthesized in good‐to‐excellent yields in a one‐pot fashion.

  羧基-MIDA-硼酸酯的应用（MIDA = N-甲基亚氨基二乙酸）作为各种钯催化转化的原位CO替代物进行了描述。先前曾证明，羧基MIDA硼酸酯是合成硼酸化杂环化合物的长凳稳定的含硼结构单元。本研究表明，羧基-MIDA-硼酸酯除了可用作杂环合成的前体外，它还是一种出色的原位CO替代物，可耐受胺，醇和碳基亲核试剂等反应性功能。在钯催化的氨基羰基化，烷氧基羰基化，羰基化的Sonogashira偶联和芳基卤化物的羰基化的Suzuki-Miyaura偶联中，突出了其广泛的官能团相容性。各种酰胺，酯，（杂）芳族炔酮
• NAMPT AND ROCK INHIBITORS
  申请人：Curtin Michael L.

  公开号：US20120122842A1

  公开（公告）日：2012-05-17

  Disclosed are compounds which inhibit the activity of NAMPT, compositions containing the compounds and methods of treating diseases during which NAMPT is expressed. Disclosed are compounds which inhibit the activity of ROCK, compositions containing the compounds and methods of treating diseases during which ROCK is expressed.

  公开了一种抑制NAMPT活性的化合物，包含该化合物的组合物和治疗NAMPT表达疾病的方法。公开了一种抑制ROCK活性的化合物，包含该化合物的组合物和治疗ROCK表达疾病的方法。
• NAMPT INHIBITORS
  申请人：AbbVie Inc.

  公开号：US20130303508A1

  公开（公告）日：2013-11-14

  Disclosed are compounds which inhibit the activity of NAMPT, compositions containing the compounds and methods of treating diseases during which NAMPT is expressed.

  本发明涉及一种抑制NAMPT活性的化合物，包括含有该化合物的组合物以及治疗NAMPT表达疾病的方法。
• Nampt and Rock Inhibitors
  申请人：AbbVie Inc.

  公开号：US20160031880A1

  公开（公告）日：2016-02-04

  Disclosed are compounds which inhibit the activity of NAMPT, compositions containing the compounds and methods of treating diseases during which NAMPT is expressed. Disclosed are compounds which inhibit the activity of ROCK, compositions containing the compounds and methods of treating diseases during which ROCK is expressed.

  本发明涉及抑制NAMPT活性的化合物、含有该化合物的组合物以及治疗表达NAMPT的疾病的方法。本发明还涉及抑制ROCK活性的化合物、含有该化合物的组合物以及治疗表达ROCK的疾病的方法。
• Fragment-based discovery of a potent NAMPT inhibitor
  作者：Alla Korepanova、Kenton L. Longenecker、Steve D. Pratt、Sanjay C. Panchal、Richard F. Clark、Marc Lake、Sujatha M. Gopalakrishnan、Diana Raich、Chaohong Sun、Andrew M. Petros

  DOI：10.1016/j.bmcl.2017.12.023

  日期：2018.2

  generate a bound pose. Based on structural insights arising from comparison of the bound fragment poses to that of bound FK866 we were able to synthetically elaborate one of the fragments into a potent NAMPT inhibitor.

  在许多癌症中，NAMPT表达均升高，使得该蛋白成为抗癌治疗的潜在靶标。我们已经针对人的NAMPT进行了基于NMR和基于TR-FRET的片段筛选，并鉴定了六种具有多种潜能的新型结合剂。对于结合到NAMPT的两个片段，获得了共晶体结构，而对于其他四个片段，则采用了力场驱动的对接来产生结合姿势。基于将结合的片段姿势与结合的FK866进行比较所获得的结构见解，我们能够将其中一个片段合成为有效的NAMPT抑制剂。