4-氨基-N-(1-苯基乙基)苯甲酰胺 | 85592-75-2

• 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-(1-苯基乙基)苯甲酰胺
• 中文别名: 苯甲酰胺,4-氨基-N-(1-苯基乙基)-
• 英文名称: 4-amino-N-(1-phenylethyl)benzamide
• CAS: 85592-75-2
• 化学式: C₁₅H₁₆N₂O
• mdl: MFCD01666807
• 分子量: 240.305
• InChiKey: LRMURALCBANCSV-UHFFFAOYSA-N

物化性质

• 沸点：
  465.8±38.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)
• 溶解度：
  >36 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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

反应信息

• 作为反应物：
  描述：

  4-氨基-N-(1-苯基乙基)苯甲酰胺 在 红铝 作用下， 以 甲苯 为溶剂， 以75%的产率得到4-[(1-Phenyl-ethylamino)-methyl]-phenylamine
  参考文献：
  名称：

  4-氨基-N-（1-苯乙基）苯甲酰胺类似物的合成和抗惊厥活性。

  摘要：

  为了研究该化合物的结构与抗惊厥活性之间的关系，制备了一组与4-氨基-N-（1-苯基乙基）苯甲酰胺有关的酰胺和胺。1氨基的酰化和烷基化导致抗惊厥活性几乎完全丧失。在4-氨基和1的芳环之间插入亚甲基会导致抗惊厥药力的轻微增加和毒性的显着增加。1中酰胺羰基的氢化物还原还产生具有抗电击引起的惊厥的ED50稍低的化合物，而在转子法中的TD50则低得多。1-苯基乙基1的修饰也降低了抗惊厥药的效力。

  DOI：

  10.1021/jm00390a016
• 作为产物：
  描述：

  p-nitro-N-(1-phenylethyl)benzamide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到4-氨基-N-(1-苯基乙基)苯甲酰胺
  参考文献：
  名称：

  一些4-氨基苯甲酰胺的抗惊厥活性。

  摘要：

  制备了一系列一些简单的伯胺和仲胺的4-氨基苯甲酰胺，并评估了其抗惊厥作用。在小鼠中对化合物进行了抗电击和戊四氮（甲唑）诱发的癫痫发作的测试，并在转子法中测试了神经功能缺损。对于所测试的那些N-烷基酰胺，4-氨基-N-戊基苯甲酰胺（6）对最大电击发作（MES）的抑制作用最强：ED50 = 42.98 mg / kg； ED50 = 42.98 mg / kg。然而，N-环己基苯甲酰胺（8）显示出最大的保护指数（PI = TD50 / ED50），为2.8。第二芳环的引入产生更有效的化合物，其中d，1-4-4-氨基-N-（α-甲基苄基）-苯甲酰胺（12）显示出最高的活性水平。腹膜内（ip）给药时，该化合物在小鼠中的抗MES ED50为18.02 mg / kg，TD50为170.78 mg / kg（PI = 9）。5）在相同的物种。这些数据与苯巴比妥和苯妥英在相同试验中的数据相比非常有利。

  DOI：

  10.1021/jm00372a013

文献信息

• Sirtuin Inhibiting Compounds
  申请人：Sinclair David A

  公开号：US20090137681A1

  公开（公告）日：2009-05-28

  Provided herein are compositions and methods for treating or preventing cancer and autoimmune diseases. Compositions comprise a sirtuin inhibitory compound that decreases the activity of a sirtuin, such as SIRT1 or Sir2. Exemplary methods comprise contacting a cell or a molecule with a sirtuin inhibitory compound that decreases the activity of a sirtuin and thereby reduces the life span of a cell, kills the cell or renders it susceptible to certain cell stresses including radiation and chemotherapy. Other methods include treating pathogens expressing a sirtuin.

  本文提供了治疗或预防癌症和自身免疫疾病的组合物和方法。组合物包括抑制sirtuin的化合物，降低sirtuin的活性，如SIRT1或Sir2。示例方法包括将细胞或分子与抑制sirtuin的化合物接触，降低sirtuin的活性，从而缩短细胞的寿命，杀死细胞或使其对包括放射治疗和化疗在内的某些细胞应激变得敏感。其他方法包括治疗表达sirtuin的病原体。
• Anti-convulsant
  申请人：Research Corporation

  公开号：US04379165A1

  公开（公告）日：1983-04-05

  New amino-benzamides and their use for the treatment of epilepsy.

  新的氨基苯甲酰胺及其用于治疗癫痫的用途。
• Iron‐Based Deep Eutectic Solvents: Key Players for Amide and Sulfonamide Synthesis and Alcohol Oxidation
  作者：Luciana Cicco、Sara Urselli、Claudia Favia、Filippo Maria Perna、Paola Vitale、Vito Capriati

  DOI：10.1002/ejoc.202400300

  日期：2024.6.24

  Selective and sustainable oxidation of secondary alcohols to their corresponding carbonyl compounds, alongside their applications as selective mono-alkylating reagents for both amide and arylsulfonamide derivatives, is achieved under aerobic and mild (40 °C) conditions in reusable Fe-based Lewis acidic deep eutectic solvents.

  在有氧和温和 (40°C) 条件下，在可重复使用的铁基路​​易斯酸性低共熔物中，实现了仲醇选择性和可持续氧化为其相应的羰基化合物，以及它们作为酰胺和芳基磺酰胺衍生物的选择性单烷基化试剂的应用溶剂。
• Design, Synthesis, and Biological Evaluation of Sirtinol Analogues as Class III Histone/Protein Deacetylase (Sirtuin) Inhibitors
  作者：Antonello Mai、Silvio Massa、Siva Lavu、Riccardo Pezzi、Silvia Simeoni、Rino Ragno、Francesca R. Mariotti、Francesco Chiani、Giorgio Camilloni、David A. Sinclair

  DOI：10.1021/jm050100l

  日期：2005.12.1

  In a search for potent inhibitors of class III histone/protein deacetylases (sirtuins), a series of sirtinol analogues have been synthesized and the degree of inhibition was assessed in vitro using recombinant yeast Sir2, human SIRT1, and human SIRT2 and in vivo with a yeast phenotypic assay. Two analogues, namely, 3- and 4-[(2-hydroxy-1-naphthalenylmethylene)amino] -N-(l-phenylethyl)benzamide (i.e., in- and p-sirtinol), were 2- to 10-fold more potent than sirtinol against human SIRT1 and SIRT2 enzymes. In yeast in vivo assay, these two small molecules were as potent as sirtinol. Compounds lacking the 2-hydroxy group at the naphthalene moiety or bearing several modifications at the benzene 2'-position of the aniline portion (carbethoxy, carboxy, and cyano) were 1.3-13 times less potent than sirtinol, whereas the 2'carboxamido analogue was totally inactive. Both (R)- and (S)-sirtinol had similar inhibitory effects on the yeast and human enzymes, demonstrating no enantioselective inhibitory effect.
• Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1
  作者：Elisabeth-Maria Bissinger、Ralf Heinke、Astrid Spannhoff、Adrien Eberlin、Eric Metzger、Vincent Cura、Pierre Hassenboehler、Jean Cavarelli、Roland Schüle、Mark T. Bedford、Wolfgang Sippl、Manfred Jung

  DOI：10.1016/j.bmc.2011.02.032

  日期：2011.6

  Arginine methylation is an epigenetic modification that receives increasing interest as it plays an important role in several diseases. This is especially true for hormone-dependent cancer, seeing that histone methylation by arginine methyltransferase I (PRMT1) is involved in the activation of sexual hormone receptors. Therefore, PRMT inhibitors are potential drugs and interesting tools for cell biology. A dapsone derivative called allantodapsone previously identified by our group served as a lead structure for inhibitor synthesis. Acylated derivatives of p-aminobenzenesulfonamides and the antilepra drug dapsone were identified as new inhibitors of PRMT1 by in vitro testing. The bis-chloroacetyl amide of dapsone selectively inhibited human PRMT1 in the low micromolar region and was selective for PRMT1 as compared to the arginine methyltransferase CARM1 and the lysine methyltransferase Set7/9. It showed anticancer activity on MCF7a and LNCaP cells and blocked androgen dependent transcription specifically in a reporter gene system. Likewise, a transcriptional block was also demonstrated in LNCaP cells using quantitative RT-PCR on the mRNA of androgen dependent genes. (C) 2011 Elsevier Ltd. All rights reserved.