benzyl (2-(phenylamino)ethyl)carbamate | 101288-83-9

• 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: benzyl (2-(phenylamino)ethyl)carbamate
• 英文别名: benzyl N-(2-anilinoethyl)carbamate
• CAS: 101288-83-9
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: YOPAHARYDNEVTE-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  477.2±38.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (2-(phenylamino)ethyl)carbamate 生成 [2-(N-benzoyl-anilino)-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Arteriovenous hemangioma involving submandibular salivary gland

  摘要：

  We present a case of an arteriovenous hemangioma involving the submandibular salivary gland in a 20 year old girl. Hemangiomas in this region are rare. Out of the reported cases most have been cavernous hemangiomas. The rarity of an arteriovenous malformation in the submandibular salivary gland prompted us to report this case.

  DOI：

  10.1007/bf02910983
• 作为产物：
  描述：

  N-Cbz-2-溴乙胺 、 苯胺 在 乙二醇 作用下， 生成 benzyl (2-(phenylamino)ethyl)carbamate
  参考文献：
  名称：

  Arteriovenous hemangioma involving submandibular salivary gland

  摘要：

  We present a case of an arteriovenous hemangioma involving the submandibular salivary gland in a 20 year old girl. Hemangiomas in this region are rare. Out of the reported cases most have been cavernous hemangiomas. The rarity of an arteriovenous malformation in the submandibular salivary gland prompted us to report this case.

  DOI：

  10.1007/bf02910983

文献信息

• Synthesis of 2-phenylthiazolidine derivatives as cardiotonic agents. IV. Modification of the phenylpiperazino moiety of 2-(phenylpiperazinoalkoxyphenyl)thiazolidine-3-carbothioamides and the corresponding carboxamides.
  作者：HIROYUKI NATE、AKISHIGE WATANABE、KENJI MATSUKI、ISAO INOUE、HISAO OHTSUKA、YASUO SEKINE、KUNIYUKI ODA、YASUSHI HONMA、AKIHIKO ISHIDA、TAKESHI KANNO、MIKIHIKO KONDA、HIDEO NAKAI、HIROSHI WADA、MIKIO TAKEDA、HIDEO YABANA、TAKU NAGAO

  DOI：10.1248/cpb.35.2825

  日期：——

  Examination of the structure-activity relationships of 2- (phenylpiperazinoalkoxyphenyl) -thiazolidine-3-carbothioamides and the corresponding carboxamides (1) as new cardiotonic agents was extended by the chemical modification of the phenylpiperazino moiety. The 4-phenylpiperidine (13), 4-phenyltetrahydropyridines (17), and related derivatives were prepared from the chlorides (10) through several intermediates (12, 14, and 16) and tested for cardiotonic activity. Generally, both the 4-phenylpiperidine (13) and 4-phenyltetrahydropyridine (17) derivatives exhibited potent positive inotropic activity comparable to that of 1. The N-phenylpiperidines (9) and amide derivatives (22, 25, and 28) exhibited no significant positive inotropy. This is also the case for the phenylpropylamines (29) and the ethylenediamines (30), which are pseudo-ring analogues of 1 with respect to the piperazine moiety. The activity of the homopiperazine derivative (23) was approximately one-thirtieth of that of the corresponding piperazine derivative (1). Thus, the presence of the six-membered, basic azacycloalkane ring (piperidine or piperazine) with a 4-phenyl group at the end of the alkoxy side chain appears to be essential for the appearance of potent positive inotropic activity in this series of compounds.

  通过对苯基哌嗪分子进行化学修饰，扩展了作为新型强心剂的 2-（苯基哌嗪烷氧基苯基）-噻唑烷-3-硫代酰胺和相应羧酰胺（1）的结构-活性关系研究。从氯化物（10）通过几个中间体（12、14 和 16）制备出了 4-苯基哌啶（13）、4-苯基四氢吡啶（17）和相关衍生物，并进行了强心活性测试。一般来说，4-苯基哌啶（13）和 4-苯基四氢吡啶（17）衍生物都表现出与 1 相似的强效正性肌力活性，而 N-苯基哌啶（9）和酰胺衍生物（22、25 和 28）则没有表现出明显的正性肌力活性。苯基丙胺（29）和乙二胺（30）的情况也是如此，它们是 1 的哌嗪分子的假环类似物。均哌嗪衍生物（23）的活性约为相应哌嗪衍生物（1）的三十分之一。因此，在这一系列化合物中，烷氧基侧链末端含有 4-苯基基团的六元碱性氮杂环烷环（哌啶或哌嗪）似乎是产生强效正性肌力活性的关键。
• Discovery of 1,5-Benzodiazepines with Peripheral Cholecystokinin (CCK-A) Receptor Agonist Activity. 1. Optimization of the Agonist “Trigger”
  作者：Christopher J. Aquino、Duncan R. Armour、Judd M. Berman、Larry S. Birkemo、Robin A. E. Carr、Dallas K. Croom、Milana Dezube、Robert W. Dougherty,、Gregory N. Ervin、Mary K. Grizzle、Julie E. Head、Gavin C. Hirst、Michael K. James、Michael F. Johnson、Laurence J. Miller、Kennedy L. Queen、Thomas J. Rimele、David N. Smith、Elizabeth E. Sugg

  DOI：10.1021/jm950626d

  日期：1996.1.1

  Directed screening of compounds selected from the Glare registry file for contractile activity on the isolated guinea pig gallbladder (GPGB) identified a series of 1,5-benzodiazepines with peripheral cholecystokinin (CCK) receptor agonist activity. Agonist efficacy within this series was modulated by variation of substituents on the N1-anilinoacetamide moiety. Remarkably, a single methyl group confers agonist activity, with an N-isopropyl substituent providing optimal efficacy. Hydrophilic substituents on the anilino nitrogen abolish agonist activity or produce antagonists of CCK. In contrast, hydrophilic electron-donating groups at the para-position of the anilino ring enhance or maintain in vitro and in vivo agonist activity. Despite decreased affinity for the human CCK-A receptor, relative to CCK-8, some of these compounds are equipotent to CCK as anorectic agents in rats following intraperitoneal administration.
• 2-Aminoadipic Acid–C(O)–Glutamate Based Prostate-Specific Membrane Antigen Ligands for Potential Use as Theranostics
  作者：Ryo Nakajima、Zora Nováková、Werner Tueckmantel、Lucia Motlová、Cyril Bařinka、Alan P. Kozikowski

  DOI：10.1021/acsmedchemlett.8b00318

  日期：2018.11.8

  The design and synthesis of prostate specific membrane antigen (PSMA) ligands derived from 2-aminoadipic acid, a building block that has not previously been used to construct PSMA. ligands, are reported. The effects of both the linker length and of an N-substituent of our PSMA ligands were probed, and X-ray structures of five of these ligands bound to PSMA were obtained. Among the ligands disclosed herein, 13b showed the highest inhibitory activity for PSMA. As ligand 13b can readily be radiolabeled since its fluorine atom is adjacent to the nitrogen atom of its pyridine ring, the use of this and related compounds as theranostics can be pursued.
• Stereoselective Synthesis of New Conformationally Restricted Analogues of a Potent CGRP Receptor Antagonist
  作者：Dmitry Zuev、Jodi A. Michne、Hong Huang、Brett R. Beno、Dedong Wu、Qi Gao、John R. Torrente、Cen Xu、Charles M. Conway、John E. Macor、Gene M. Dubowchik

  DOI：10.1021/ol0510062

  日期：2005.6.1

  A stereocontrolled racemic synthesis of conformationally restricted analogues 2a and 2b of a potent CGRP receptor antagonist 1 by novel functionalization of 2-substituted octahydropyrido[1,2-a]pyrazin-6-ones is described. The new diastereoselective LDA-promoted α-nitration of intermediate lactams established the required trans-configuration in the desired products.