N-环己基氨基甲酰肼 | 52662-76-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-环己基氨基甲酰肼
• 中文别名: N-环己基氨基脲盐酸盐；3-氨基-1-环己基-脲
• 英文名称: 4-Cyclohexyl-semicarbazid
• 英文别名: N-cyclohexylhydrazinecarboxamide；4-cyclohexylsemicarbazide；1-amino-3-cyclohexylurea
• CAS: 52662-76-7
• 化学式: C₇H₁₅N₃O
• mdl: MFCD00885252
• 分子量: 157.216
• InChiKey: VZVGVHNZWUQMRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N-环己基氨基甲酰肼 在 ammonium hydroxide 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 22.0h， 生成 2-(3-cyclohexylaminocarbonyltriazene-1-yl)adenosine
  参考文献：
  名称：

  N⁶-Cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a Very Selective Agonist with High Affinity for the Human Adenosine A₁ Receptor

  摘要：

  Four subtypes of adenosine receptors are currently known, that is, A(1), A(2A), A(2B), and A(3) receptors. Interestingly, quite substantial species differences exist especially between human and rat A(3) receptors. As a result, ligands such as CCPA, which are very selective for the rat A(1) and A(3) receptor versus the human A(3) receptor, are substantially less selective when the human A(1) and A(3) receptors are compared. New 2-substituted and 2,N-6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A(1), A(2A), A(2B), and A(3) receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A(2A) receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A(1) receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 +/- 1.3 nM for the human adenosine A(1) receptor. Introduction of a diphenethyl substituent at the N-6-position of this compound resulted in a high-affinity agonist, 3.1 +/- 0.9 nM, for the human adenosine A(1) receptor with 316- and 45-fold selectivity versus the human A(2A) and human A(3) receptors, respectively. The most selective, high-affinity human adenosine A(1) receptor agonist was the disubstituted compound N-6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 +/- 0.8 nM for the human adenosine A, receptor and was 75-fold and 214-fold selective versus the human A(2A) and human A(3) receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A(1) receptor with an IC50 of 1.5 +/- 0.5 nM.

  DOI：

  10.1021/jm021074j
• 作为产物：
  描述：

  环己基异氰酸酯 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到N-环己基氨基甲酰肼
  参考文献：
  名称：

  N⁶-Cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a Very Selective Agonist with High Affinity for the Human Adenosine A₁ Receptor

  摘要：

  Four subtypes of adenosine receptors are currently known, that is, A(1), A(2A), A(2B), and A(3) receptors. Interestingly, quite substantial species differences exist especially between human and rat A(3) receptors. As a result, ligands such as CCPA, which are very selective for the rat A(1) and A(3) receptor versus the human A(3) receptor, are substantially less selective when the human A(1) and A(3) receptors are compared. New 2-substituted and 2,N-6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A(1), A(2A), A(2B), and A(3) receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A(2A) receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A(1) receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 +/- 1.3 nM for the human adenosine A(1) receptor. Introduction of a diphenethyl substituent at the N-6-position of this compound resulted in a high-affinity agonist, 3.1 +/- 0.9 nM, for the human adenosine A(1) receptor with 316- and 45-fold selectivity versus the human A(2A) and human A(3) receptors, respectively. The most selective, high-affinity human adenosine A(1) receptor agonist was the disubstituted compound N-6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 +/- 0.8 nM for the human adenosine A, receptor and was 75-fold and 214-fold selective versus the human A(2A) and human A(3) receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A(1) receptor with an IC50 of 1.5 +/- 0.5 nM.

  DOI：

  10.1021/jm021074j

文献信息

• Copper-Catalyzed Oxidative Carbamoylation of <i>N</i> -Arylacrylamides with Hydrazinecarboxamides Leading to 2-(Oxindol-3-yl)acetamide<b>s</b>
  作者：Zeng-Yang He、Jing-Yu Guo、Shi-Kai Tian

  DOI：10.1002/adsc.201800012

  日期：2018.4.3

  radical carbamoylation/cyclization reaction of N‐arylacrylamides with hydrazinecarboxamides has been developed for facile access to 2‐(oxindol‐3‐yl)acetamides, which had been utilized as precursors in the synthesis of natural bioactive pyrrolidinoindolines. In the presence of 1 mol% of copper(II) carbonate and 4 equiv. of tert‐butyl hydroperoxide, a wide range of N‐arylacrylamides underwent highly regioselective

  已开发出N-芳基丙烯酰胺与肼甲酰胺的串联氨基甲酰化/环化反应，可轻松获得2-（oxindol-3-yl）乙酰胺，后者已被用作天然生物活性吡咯烷二氢吲哚的合成前体。在1摩尔％的碳酸铜（II）和4当量的存在下。在叔丁基过氧化氢中，广泛的N-芳基丙烯酰胺与肼甲酰胺进行了高度区域选择性的氨基甲酰基化反应，然后进行5-exo-trig环化反应，从而以中等至优异的收率得到结构多样的2-（oxindol-3-yl）乙酰胺。
• A novel type of nonsteroidal estrone sulfatase inhibitors
  作者：Peter Jütten、Winfried Schumann、Albert Härtl、Lothar Heinisch、Udo Gräfe、Walter Werner、Hermann Ulbricht

  DOI：10.1016/s0960-894x(02)00171-3

  日期：2002.5

  structure-activity relationships of our study into a series of thiosemicarbazone derivatives of madurahydroxylactone as potential nonsteroidal inhibitors of the enzyme estrone sulfatase. The most active compound, the cyclohexylthiosemicarbazone, was shown to be a non-competitive inhibitor with a K(i) of 0.35microM. This compound is devoid of estrogenic properties and showed low acute toxicity in the hen's

  马杜拉羟基内酯（MHL）是土壤细菌野紫菜（Nonomuria rubra）产生的次生代谢产物，属于苯并[a]萘并醌类。我们报告的初步结果和我们的研究成一系列的马杜拉羟基内酯的硫半脲衍生物作为潜在的非甾体类雌激素硫酸酯酶抑制剂的结构活性关系。活性最高的化合物，环己基硫代半脲，显示为非竞争性抑制剂，K（i）为0.35microM。该化合物缺乏雌激素特性，在母鸡的可育卵筛查试验中显示出较低的急性毒性。
• 1-Substituted carbamoyl and thiocarbamoyl-4,5-dihydro-1H-pyrazoles as possible cytotoxic and antimicrobial agents
  作者：Khalid A. Khan、Hassan M. Faidallah

  DOI：10.3109/14756366.2015.1057717

  日期：2016.7.3

  appropriate isocyanate and isothiocyanate respectively, or alternatively by condensing the appropriate diketone with the proper substituted semicarbazide or thiosemicarbazide. The structures of the prepared compounds were fully determined by analytical and spectral methods. Preliminary biological screening of the prepared compounds revealed significant antibacterial and cytotoxic activities for some compounds

  通过分别用适当的异氰酸酯和异硫氰酸酯处理相应的吡唑，或通过将适当的二酮与适当的取代的氨基脲或硫代氨基脲缩合来制备两个系列的1-取代的氨基甲酰基和硫代氨基甲酰基衍生物。通过分析和光谱方法完全确定了所制备化合物的结构。对制备的化合物进行的初步生物学筛选显示，某些化合物具有显着的抗菌和细胞毒性活性。发现化合物4a2和4a3对人结肠癌HT29（分别为11.8和7.5μg/ mL）和人乳腺癌MCF 7（分别为3.4和2.6μg/ mL）最具活性。构效关系（SAR）和计算机病毒相关属性（HBD，HBA，tPSA，
• Direct Carbamoylation of Quinoline N‐oxides with Hydrazinecarboxamides via C‐H Bond Activation Catalyzed by Copper Catalyst
  作者：Zu-Li Wang、guanghui li、Dao-Qing Dong、yun yang、xianyong yu

  DOI：10.1002/adsc.201801430

  日期：——

  An efficient method for the carbamoylation of quinoline N‐oxides catalyzed by copper was developed. A variety of quinoline N‐oxides and hydrazinecarboxamides with different groups was well tolerated in this system.

  开发了一种有效的铜催化喹啉N-氧化物氨基甲酰化的方法。该系统对各种具有不同基团的喹啉N-氧化物和肼甲酰胺具有很好的耐受性。
• A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions
  作者：Kazuyuki Tokumaru、Jeffrey N. Johnston

  DOI：10.1039/c7sc00195a

  日期：——

  aromatic heterocycle valued for its low-lipophilicity in drug development. Substituents at the 2- and/or 5-positions can modulate the heterocycle's electronic and hydrogen bond-accepting capability, while exploiting its use as a carbonyl bioisostere. A new approach to 1,3,4-oxadiazoles is described wherein α-bromo nitroalkanes are coupled to acyl hydrazides to deliver the 2,5-disubstituted oxadiazole directly

  1,3,4-恶二唑是一种芳香杂环，因其低亲脂性而在药物开发中具有重要价值。2-和/或5-位的取代基可以调节杂环的电子和氢键接受能力，同时利用其作为羰基生物等排体的用途。描述了一种制备 1,3,4-恶二唑的新方法，其中 α-溴硝基烷烃与酰肼偶联以直接提供 2,5-二取代恶二唑，避免了 1,2-二酰肼中间体。通过利用手性 α-溴硝基烷或氨基酸酰肼底物，可以改善恶二唑取代仲胺新结构单元的获得。与依赖高亲氧性试剂来实现不对称 1,2-二酰肼环化的替代方案相比，恶二唑合成的非脱水条件尤其值得注意。通过标准水洗直接去除副产物，打破了温和的条件。