cyclohexylcarbamoylmethylcarbamic acid benzyl ester | 3496-41-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cyclohexylcarbamoylmethylcarbamic acid benzyl ester
• 英文别名: N-benzyloxycarbonyl-glycine cyclohexylamide；N-Benzyloxycarbonyl-glycin-cyclohexylamid；benzyl N-[2-(cyclohexylamino)-2-oxoethyl]carbamate
• CAS: 3496-41-1
• 化学式: C₁₆H₂₂N₂O₃
• 分子量: 290.362
• InChiKey: PBAJOLIZPIQEPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyclohexylcarbamoylmethylcarbamic acid benzyl ester 在 氯仿 、 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 生成 N-(N-benzoyl-α-glutamyl)-glycine cyclohexylamide
  参考文献：
  名称：

  Distress and disease status among patients with rheumatoid arthritis: Roles of coping styles and perceived responses from support providers

  摘要：

  Previous research has shown that social support can have a beneficial impact on coping processes and psychological adjustment in patients with rheumatoid arthritis (RA). The association of individual coping styles and perceived responses from others to one's pain episodes with patients' distress and disease status over time was investigated. The sample consisted of 42 middle-aged patients with RA who were predominantly White (98%), female (64%), and married (88%). Participants completed surveys and their rheumatologist completed clinical assessments of patient disease status at 2 time points over a 9-month period Although punishing responses from others (e.g, getting irritated or angry when the patient is in pain) were perceived as relatively infrequent, they were associated with a patient coping style of focusing on and venting of negative emotion as well as elevated negative affect (NA). Findings also indicated that those who perceived punishing responses from close others and coped by venting negative emotions reported increased NA over time and were rated by their rheumatologist as having more severe RA disease status over time. Implications for psychosocial intervention and directions for future research are discussed.

  DOI：

  10.1207/s15324796abm2302_8
• 作为产物：
  描述：

  N-苄氧羰基甘氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 cyclohexylcarbamoylmethylcarbamic acid benzyl ester
  参考文献：
  名称：

  N-保护氨基酸的非活性酯的催化剂和无溶剂酰胺化

  摘要：

  在温和的反应条件下，证明了由N保护的氨基酸和各种胺的非活性酯制备酰胺的无催化剂方法。我们努力回收过量的胺和生成的醇是一种在简单的操作条件下实现环境友好且具有成本效益的合成方法。

  DOI：

  10.1016/j.tetlet.2011.03.039

文献信息

• Active site mapping of trypsin, thrombin and matriptase-2 by sulfamoyl benzamidines
  作者：Stefan Dosa、Marit Stirnberg、Verena Lülsdorff、Daniela Häußler、Eva Maurer、Michael Gütschow

  DOI：10.1016/j.bmc.2012.08.042

  日期：2012.11

  approach was performed with these inhibitors to scan the active site of the three target proteases. In particular, bisbenzamidines, able to interact with both the S1 and S3/S4 binding sites, showed notable affinity. In branched bisbenzamidines 66–73 containing a third hydrophobic residue, opposite effects of the stereochemistry on trypsin and thrombin inhibition were observed.

  苯甲idine部分是一种众所周知的精氨酸模拟物，已被引入多种配体中，包括胰蛋白酶样丝氨酸蛋白酶的拟肽抑制剂。根据它们的主要底物特异性，苄am残基与此类酶的S1口袋底部的带负电荷的天冬氨酸相互作用。六个系列的苯甲脒衍生物（的1 - 73）的合成和评价作为两个原型丝氨酸蛋白酶的抑制剂，即，牛胰蛋白酶和人凝血酶。作为进一步的靶标，研究了人Matriptase-2（一种最近发现的II型跨膜丝氨酸蛋白酶）。Matriptase-2通过下调铁调素表达在铁稳态中代表了重要的调节蛋白酶。化合物1 –73个分子被设计为包含一个固定的氨磺酰基苯甲酰胺部分作为精氨酸模拟物和一个连接有连接子的附加亚结构，例如叔丁酯，羧酸盐或第二个苯甲idine官能团。用这些抑制剂进行了系统的作图方法，以扫描三种靶蛋白酶的活性位点。特别地，能够与S1和S3 / S4结合位点相互作用的双苯甲m显示出显着的亲和力。在支链bisbenzamidines
• Ethyl 2-(<i>tert</i>-Butoxycarbonyloxyimino)-2-cyanoacetate (Boc-Oxyma) as Coupling Reagent for Racemization-Free Esterification, Thioesterification, Amidation and Peptide Synthesis
  作者：Kishore Thalluri、Krishna Chaitanya Nadimpally、Maharishi Parasar Chakravarty、Ashim Paul、Bhubaneswar Mandal

  DOI：10.1002/adsc.201200645

  日期：2013.2.1

  the synthesis and utility of ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate (Boc-Oxyma) as an efficient coupling reagent for racemization-free esterification, thioesterification, amidation reactions and peptide synthesis that uses equimolar amounts of acids and alcohols, thiols, amines or amino acids, respectively. Its application to solid phase as well as solution phase peptide synthesis is also

  在这里，我们报告2-（叔丁氧基羰基氧基亚氨基）-2-氰基乙酸乙酯（Boc-Oxyma）的合成和实用性，该化合物是用于等消旋酯化，硫代酯化，酰胺化反应和使用等摩尔量的酸和分别是醇，硫醇，胺或氨基酸。还证明了其在固相以及溶液相肽合成中的应用，并讨论了机理研究。就其高反应性和作用机理而言，Boc-氧化酶类似于众所周知的偶联剂COMU 1- [1-氰基-2-乙氧基-2-氧代亚乙基亚氨基氧基）-二甲基氨基吗啉代]六氟磷酸uro}。但是，它不仅易于制备，而且易于回收和再利用，从而产生的化学废物少得多。
• <i>N</i>-(Benzyloxycarbonyl)glycine Esters and Amides as New Anticonvulsants
  作者：Muriel Geurts、Jacques H. Poupaert、Gerhard K. E. Scriba、Didier M. Lambert

  DOI：10.1021/jm970086f

  日期：1998.1.1

  neutral amino acid exhibiting weak anticonvulsant activities in vivo. Recently, studies have demonstrated that N-(benzyloxycarbonyl)glycine (1) antagonized seizures superior to glycine in addition to activity in the maximal electroshock (MES) test, a convulsive model where glycine is inactive. In the present study a series of ester and amide derivatives of 1 as well as esters of N-(3-phenylpropanoyl)glycine

  甘氨酸是一种小的中性氨基酸，在体内表现出弱的抗惊厥活性。最近，研究表明，在最大电击（MES）测试（一种甘氨酸失活的惊厥模型）中，N-（苄氧羰基）甘氨酸（1）对抗癫痫发作的作用优于甘氨酸。在本研究中，已经制备了一系列的1的酯和酰胺衍生物以及N-（3-苯基丙酰基）甘氨酸的酯（5）。在MES测试以及几种化学诱导的癫痫发作模型中对化合物进行了评估。在所研究的衍生物中，N-（苄氧基羰基）甘氨酸苄酰胺（16）是最有效的化合物，在MES试验中表现出与药物苯妥英相当的抗惊厥活性。腹腔注射后30分钟和3小时测定的中位有效剂量（ED50）为4.8和11.6 mg / kg 行政管理。化合物16还可以在不同的化学诱导模型（例如士的宁，3-巯基丙酸和戊四唑测试）中有效抑制强直性癫痫发作。此外，在150 mg / kg的剂量下，在转子试验中，此处研究的化合物未显示急性神经毒性。结论是，N-（苄氧基羰基）甘氨酸酰胺，特别是16种，是有效的抗惊厥药。
• Amidine compounds
  申请人：JAPAN TOBACCO INC.

  公开号：US20040006099A1

  公开（公告）日：2004-01-08

  A compound of the formula [I] 1 wherein R 1 , R 2 and R 3 are the same or different and each is hydrogen atom, hydroxy, lower alkyl or aryl, R is a group of the formula 2 wherein each symbol is as defined in the specification, a salt thereof or a prodrug thereof. The compound of the present invention, a salt thereof and a prodrug thereof are useful as factor Xa inhibitor and blood coagulation inhibitor, and are useful for the prophylaxis and/or treatment of diseases caused by blood coagulation or thrombus.

  化合物的式子为[I]1，其中R1、R2和R3相同或不同，且每个都是氢原子、羟基、低碳基或芳基，R是式子2的基团，其中每个符号如规范中定义的那样，其盐或前药。本发明的化合物、其盐和前药可用作因子Xa抑制剂和血液凝固抑制剂，并可用于预防和/或治疗由血液凝固或血栓引起的疾病。
• Bacterial enzyme inhibitors
  申请人：Gane Paul

  公开号：US20050182137A1

  公开（公告）日：2005-08-18

  Compounds of formula (I), are antibacterial agents, wherein: Z represents a radical formula —N(OH)CH(═O) or of formula —C(═O)NH(OH); X represents a straight or branched divalent C 1 -C 6 alkenylene, or C 2 -C 6 alkynylene radical; n is O or 1; and R represents an optionally substituted carbocyclic or heterocyclic group.

  公式（I）的化合物是抗菌剂，其中：Z代表基团公式—N（OH）CH（═O）或公式—C（═O）NH（OH）; X代表直链或支链的二价C1-C6烯基或C2-C6炔基基团; n为O或1; R代表可选取代的碳环或杂环基团。