(E)-2-(1-(4-chlorophenyl)ethylidene)hydrazine-1-carboximidamide | 132685-72-4

• 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: (E)-2-(1-(4-chlorophenyl)ethylidene)hydrazine-1-carboximidamide
• 英文别名: 2-[(E)-1-(4-chlorophenyl)ethylideneamino]guanidine
• CAS: 132685-72-4
• 化学式: C₉H₁₁ClN₄
• 分子量: 210.666
• InChiKey: NBHBAGUAKHKQAS-AWNIVKPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-氰基甲亚胺乙酯 、 (E)-2-(1-(4-chlorophenyl)ethylidene)hydrazine-1-carboximidamide 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以67%的产率得到N-[amino-[2-[1-(4-chlorophenyl)ethylidene]hydrazinyl]methylidene]-N'-cyanomethanimidamide
  参考文献：
  名称：

  Miyamoto, Yoshiko; Yamazaki, Chiji; Matzui, Megumi, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 6, p. 1553 - 1557

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯乙酮 、 肼甲酰亚胺酰胺一氯化氢 以 水 为溶剂， 生成 (E)-2-(1-(4-chlorophenyl)ethylidene)hydrazine-1-carboximidamide
  参考文献：
  名称：

  咪唑基腙作为有效的抗结肠癌药物：设计、合成、生物学评价和计算研究

  摘要：

  含有咪唑和腙结构框架的化合物已被广泛研究并证明具有广泛的药理学特性。在这项研究中，通过多步化学反应设计并合成了一系列由咪唑环和腙部分组成的 20 种新型杂化化合物。合成的化合物通过各种光谱技术进行表征，包括 FT-IR、1H NMR、13C NMR 和 HRMS。此外，所提出的结构通过单晶X射线分析得到了解析。对这些化合物的体外抗结肠癌活性进行了评估，最有前途的化合物（即 和 ）表现出显着的剂量和时间依赖性细胞毒性，并对 HT-29 和 HCT-116 细胞具有选择性。此外，还进行了分子对接、分子动力学模拟和结合自由能分析，以更好地了解潜在抗癌药物的构效关系和作用机制。我们的初步研究结果表明，化合物 和 可以被用作进一步抗癌药物开发的主要结构。

  DOI：

  10.1016/j.molstruc.2024.139240

文献信息

• Gram‐Positive and Gram‐Negative Antibiotic Activity of Asymmetric and Monomeric Robenidine Analogues
  作者：Cecilia C. Russell、Andrew Stevens、Hongfei Pi、Manouchehr Khazandi、Abiodun D. Ogunniyi、Kelly A. Young、Jennifer R. Baker、Siobhann N. McCluskey、Stephen W. Page、Darren J. Trott、Adam McCluskey

  DOI：10.1002/cmdc.201800463

  日期：2018.12.6

  except with concomitant introduction of an imine C‐alkyl group. The activity of these analogues against MRSA and VRE ranged from 8 μg mL−1 to inactive (MIC>128 μg mL−1) with the naphthyl and indole analogues. Gram‐negative activity was most promising with two compounds at 16 μg mL−1 against E. coli. Against P. aeruginosa, the highest activity observed was with MIC values of 32 μg mL−1 with another two analogues

  罗非替丁的去对称化（1：N '，2-二（（E）-4-氯苄叉）肼-1-羧酰亚胺肼）和亚胺烷基取代基的引入具有良好的抗生素活性。值得注意的是，两种类似物对耐万古霉素的肠球菌（VRE）的效力有所提高，其中一种的MIC为0.5μgmL -1。发现有五个类似物比铅1具有更强的效价。吲哚部分的引入导致针对甲氧西林抗性金黄色葡萄球菌（MRSA）的活性最强的robenidine类似物，MIC为1.0μgmL -1。亚胺C = NH等位基因（C = O / C = S）不活跃。单体类似物为16–64μgmL-1对MRSA和VRE有效。缺少末端酰肼NH部分的类似物在64μgmL -1下显示适度的革兰氏阴性活性。研究表明，在16–64μgmL -1下， 4-叔丁基类似物对革兰氏阳性和阴性菌株均具有活性。通常，除伴随引入亚胺C-烷基外，对芳香族基团的其他修饰耐受性差。这些类似物对MRSA和VRE的活性范围为8μgmL
• Synthesis of aryl-hydrazones via ultrasound irradiation in aqueous medium
  作者：Ana Cristina Lima Leite、Diogo Rodrigo de M. Moreira、Lucas Cunha Duarte Coelho、Frederico Duarte de Menezes、Dalci José Brondani

  DOI：10.1016/j.tetlet.2007.12.103

  日期：2008.2

  The synthesis of aryl-hydrazones from aromatic aldehydes/ketones and hydrazides (semicarbazide, thiosemicarbazide and aminoguanidine) is described using aqueous medium (acid conditions) under ultrasound irradiation with short reaction times (20–30 min), the reactions occurring at room temperature and giving rise to good to excellent yields of the products, along with the diastereoselectivities. The

  描述了使用水性介质（酸性条件）在短时间（20-30分钟）超声辐照下，由芳族醛/酮和酰肼（氨基脲，氨基脲和氨基胍）合成芳基hydr的反应，该反应发生在室温和与非对映选择性一起产生了很好的产品收率。程序也简单干净。
• Synthesis, structure investigations, and antimicrobial activity of selected s-trans-6-aryl-4-isopropyl-2-{2-[(E)-1-phenylalkylidene]-(E)-hydrazino}-1,4-dihydropyrimidine hydrochlorides
  作者：Edith Gößnitzer、Gebhard Feierl、Ute Wagner

  DOI：10.1016/s0928-0987(01)00202-0

  日期：2002.2

  A series of 6-aryl-4-isopropyl-2-[2-(1-phenylalkylidene)hydrazino]-1,4-dihydropyrimidine hydrochlorides was prepared and tested for antibacterial and antifungal effects. The title compounds were synthesized by cyclocondensation of N-2-(1-phenylalkylideneamino)guanidines with 1-aryl-4-methyl-2-penten-1-ones. Structure analyses of the prepared compounds were accomplished by means of 1D and 2D NMR spectroscopy. The analyses showed that the ring closure reaction took place regioselectively in all cases and generated exclusively 2-(phenylalkylidenehydrazino)dihydropyrimidines. According to the NOE experiments, the applied N-2-(1- phenylalkylideneamino)guanidines exist in [D-o]DMSO solution as s-trans-(E)- and the title compounds as s-trans-(E,E)-isomers. The antimicrobial activity was evaluated against representative Gram-negative and Gram-positive bacteria, and against the pathogenic yeast Candida albicans, The tested title compounds showed weak antibacterial activity against Gram-positive bacteria, and one compound was active against Candida albicans. (C) 2002 Elsevier Science B.V. All rights reserved.
• COMPOUNDS AND METHODS OF TREATING INFECTIONS
  申请人：Neoculi Pty Ltd

  公开号：EP2991968B1

  公开（公告）日：2021-11-10
• METHODS FOR TREATING PROTOZOAN INFECTIONS
  申请人：Neoculi Pty Ltd.

  公开号：US20170291886A1

  公开（公告）日：2017-10-12

  The invention provides compounds of Formula (I), and their use in methods for treating or preventing a protozoan infection in a subject using a compound of Formula (I). The invention also provides the use of a compound of Formula (I) in the manufacture of a medicament for the treatment of a protozoan infection in a subject. The invention further provides a medical device when used in a method of treating or preventing a protozoan infection in a subject and to a medical device comprising the composition of the invention.