4-氨基-N-苄基苯甲酰胺 | 54977-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氨基-N-苄基苯甲酰胺
• 中文别名: 苯甲酰胺,4-氨基-N-苯基甲基-；4-氨基-N-(苯基甲基)苯甲酰胺；苯甲酰胺,4-氨基-N-苄基-
• 英文名称: 4-amino-N-benzylbenzamide
• CAS: 54977-92-3
• 化学式: C₁₄H₁₄N₂O
• mdl: MFCD00440145
• 分子量: 226.278
• InChiKey: ZWMQLNXGNSNUEO-UHFFFAOYSA-N

物化性质

• 溶解度：
  >33.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  4-氨基-N-苄基苯甲酰胺 在 sodium cyanoborohydride 作用下， 以 甲醇 、 苯 为溶剂， 反应 26.5h， 生成 N-Benzyl-4-(2,5-dihydroxy-benzylamino)-benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of a Series of Lavendustin A Analogues That Inhibit EGFR and Syk Tyrosine Kinases, as Well as Tubulin Polymerization

  摘要：

  A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibition of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several compounds in the series were effective inhibitors of both kinases, it seemed questionable whether their inhibitory effects on these kinases were responsible for the cytotoxic properties observed in a variety of human cancer cell cultures. Accordingly, a COMPARE analysis of the cytotoxicity profile of the most cytotoxic member of the series was performed, and the results indicated that its cytotoxicity profile was similar to that of antitubulin agents. This mechanism of action was supported by demonstrating that most compounds in the series were moderately effective as inhibitors of tubulin polymerization. This suggests that the lavendustin A analogues reported here, as well as some of the previously reported lavendustin A analogues, may be acting as cytotoxic agents by a mechanism involving the inhibition of tubulin polymerization.

  DOI：

  10.1021/jm000387g
• 作为产物：
  描述：

  N-BOC-4-氨基苯甲酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-氨基-N-苄基苯甲酰胺
  参考文献：
  名称：

  新型基于恶唑烷酮的过氧化物酶体增殖物激活受体激动剂：分子建模，合成和生物学评估。

  摘要：

  按照公认的三模块结构设计了一系列新的过氧化物酶体增殖物激活受体（PPAR）手性配体，该结构包括极性头，接头和疏水尾。大多数配体都将恶唑烷酮部分掺入作为新型极性头，并且疏水性尾部的性质也有所变化。已经使用结合到PPARα受体的配体结合结构域的激动剂的晶体结构进行了对接研究，作为其设计的工具。已经开发了合适​​的合成方法，并且已经制备了具有不同立体化学的化合物。对基础和配体诱导的活性的评估证明，几种化合物对PPARα受体表现出激动剂活性，从而验证了恶唑烷酮模板的PPAR活性。此外，还有两种化合物图2和图4显示了PPARα/PPARγ的双重激动作用和大鼠有趣的食物摄入减少。

  DOI：

  10.1021/acs.jmedchem.5b00849

文献信息

• Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support
  作者：Andrea Ojeda-Porras、Alejandra Hernández-Santana、Diego Gamba-Sánchez

  DOI：10.1039/c5gc00189g

  日期：——

  A highly improved and green methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. The scope of this...

  描述了使用硅胶作为固体载体和催化剂将羧酸与胺直接酰胺化的高度改进的绿色方法。这个范围...
• Significance of reagent addition sequence in the amidation of carboxylic acids mediated by PPh₃ and I₂
  作者：Sirilak Wangngae、Chuthamat Duangkamol、Mookda Pattarawarapan、Wong Phakhodee

  DOI：10.1039/c5ra03184b

  日期：——

  The outcome of the amidation reaction mediated by PPh₃–I₂ was found to be highly dependent on the addition sequence of the reagents.

  PPh3-I2介导的酰胺化反应的结果被发现高度依赖试剂的加入顺序。
• Fused heterocyclic compounds useful as kinase modulators
  申请人：Vaccaro Wayne

  公开号：US20070078136A1

  公开（公告）日：2007-04-05

  Compounds having the formula (1), and enantiomers, and diastereomers, pharmaceutically-acceptable salts, thereof, are usefuil as kinase modulators, including MK2 modulation, wherein one of E and F is a nitrogen atom and the other of E and F is a carbon atom, Z is N or CR 3 , and R 1 , R 2 , R 3 , X and Y are as defined herein.

  具有化学式（1）的化合物，以及其对映体、非对映体、药用可接受的盐，可用作激酶调节剂，包括MK2调节，其中E和F中的一个是氮原子，另一个是碳原子，Z是N或CR3，R1、R2、R3、X和Y如本文所定义。
• Graphene Oxide: A Metal‐Free Carbocatalyst for the Synthesis of Diverse Amides under Solvent‐Free Conditions
  作者：Khushbu P. Patel、Eknath M. Gayakwad、Vilas V. Patil、Ganapati S. Shankarling

  DOI：10.1002/adsc.201801673

  日期：2019.4.23

  solvent‐free reaction conditions providing desired products in good to excellent yields. The one‐pot synthesis of 2,3‐Dihydro‐5H‐benzo[b]‐1,4‐thiazepin‐4‐one moiety by GO catalyzed Aza Michael addition followed by intramolecular transamidation is also described. A plausible reaction mechanistic pathway involving H‐bonding is discussed. The graphene oxide can be recycled and reused up to five cycles without

  证明了环保，廉价，碳催化剂，氧化石墨烯（GO）促进了各种羧酰胺与脂肪族，环状和芳香族胺的高效无金属氨基转移。该协议同样适用于邻苯二甲酰亚胺，尿素和硫代酰胺，以确定其适应性。存在于氧化石墨烯表面的羰基（-C = O），环氧（-O-），羧基（-COOH）和羟基（-OH）等氧化官能团赋予催化剂酸性。氧化石墨烯本质上是多相的，可以在无溶剂的反应条件下有效地工作，从而以高至优异的收率提供所需的产物。还描述了GO催化的Aza Michael加成反应，然后进行分子内氨基转移，一锅法合成2,3-二氢-5H-苯并[b] -1,4-噻吩并-4-酮部分。讨论了涉及氢键的可能的反应机理途径。氧化石墨烯可以循环使用多达五个周期，而催化活性却没有太大损失。
• The reduction of aromatic nitro groups on solid supports using sodium hydrosulfite (Na2S2O4)
  作者：Randall A Scheuerman、David Tumelty

  DOI：10.1016/s0040-4039(00)00959-x

  日期：2000.8

  An improved method for reducing aromatic nitro compounds on solid-phase supports using sodium hydrosulfite is presented. Conditions have been optimized to enable the use of this reagent for reductions on both polyethyleneglycol-polystyrene (PEG) resins and traditional polystyrene (PS) resins.

  提出了一种使用亚硫酸氢钠还原固相载体上芳族硝基化合物的改进方法。已对条件进行了优化，以使该试剂可用于还原聚乙二醇-聚苯乙烯（PEG）树脂和传统聚苯乙烯（PS）树脂。