p-Chlorobenzylidenaminoguanidine hydrochloride | 6933-71-7

• 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: p-Chlorobenzylidenaminoguanidine hydrochloride
• 英文别名: (4-chloro-benzylidenamino)guanidine hydrochloride；4-chlorobenzaldehyde guanylhydrazone hydrochloride；JR-220；1-(4-Chlorobenzylideneamino)guanidine Hydrochloride；2-[(4-chlorophenyl)methylideneamino]guanidine;hydrochloride
• CAS: 6933-71-7
• 化学式: C₈H₉ClN₄*ClH
• 分子量: 233.1
• InChiKey: MYGZIWITMJYYMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.8
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 肼甲酰亚胺酰胺一氯化氢 以 乙醇 为溶剂， 反应 5.0h， 生成 p-Chlorobenzylidenaminoguanidine hydrochloride
  参考文献：
  名称：

  氨基胍Hy衍生物作为非肽NPFF1受体拮抗剂可逆阿片类药物引起的痛觉过敏。

  摘要：

  先前已显示神经肽FF受体（NPFF1R和NPFF2R）及其内源性配体神经肽FF具有抗阿片类药物的特性，并且在鸦片类药物长期服用相关的不良反应中起关键作用，包括阿片类药物引起的痛觉过敏和镇痛耐受性的发展。在这项工作中，我们试图通过将我们的注意力集中在一系列杂环上来鉴定新的NPFF受体配体，这些杂环作为刚性化的非肽NPFF受体配体，从已经描述的氨基胍（AGH）开始。结合实验和功能测定突出了用于体内实验的AGH 1n及其刚性化类似物2-氨基-二氢嘧啶22e。如先前使用原型二肽拮抗剂RF9所示，1n和22e均显着降低了芬太尼诱导的鼠持久性痛觉过敏。总而言之，这些数据表明，AGH硬化对两种NPFF受体均保持纳摩尔亲和力，同时改善了对NPFF1R的拮抗特性。

  DOI：

  10.1021/acschemneuro.8b00099

文献信息

• Treating neuropathic pain with neuropeptide FF receptor 2 agonists
  申请人：Scully L. Audra

  公开号：US20050136444A1

  公开（公告）日：2005-06-23

  The invention described below relates to the discovery of the neuropeptide FF receptor subtype that mediates acute nociception and chronic neuropathic pain, compounds that selectively interact with this receptor subtype and methods for treating acute pain and chronic neuropathic pain.

  以下所描述的发明涉及到发现了介导急性痛觉和慢性神经病理性疼痛的神经肽FF受体亚型、与该受体亚型有选择性相互作用的化合物以及治疗急性疼痛和慢性神经病理性疼痛的方法。
• Evaluation of guanylhydrazone derivatives as inhibitors of Candida rugosa digestive lipase: Biological, biophysical, theoretical studies and biotechnological application
  作者：Camilla C. Santana、Edeíldo F. Silva-Júnior、João César N. Santos、Érica E. da S. Rodrigues、Isabella M. da Silva、João X. Araújo-Júnior、Ticiano G. do Nascimento、Leandro A. Oliveira Barbosa、Camila B. Dornelas、Isis M. Figueiredo、Josué Carinhanha C. Santos、Luciano Aparecido M. Grillo

  DOI：10.1016/j.bioorg.2019.03.030

  日期：2019.6

  This work aimed to evaluate the inhibition of Candida rugosa lipase by five guanylhydrazone derivatives through biological, biophysical and theoretical studies simulating physiologic conditions. The compound LQM11 (IC50 = 14.70 mu M) presented the highest inhibition against the enzyme. Therefore, for a better understanding of the interaction process, spectroscopic and theoretical studies were performed. Fluorescence and UV-vis assays indicate a static quenching mechanism with non-fluorescent supramolecular complex formation and changing the native protein structure. The binding process was spontaneous (Delta G < 0) and electrostatic forces (Delta H < 0 and Delta S > 0) played a preferential role in stabilizing the complex ligand-lipase. The compounds were classified as non-competitive inhibitors using orlistat as a reference in competition studies. Based on the H-1 NMR assays it was possible to propose the sites of ligand (epitope) that bind preferentially to the enzyme and the theoretical studies were consistent with the experimental results. Finally, LQM11 was efficient as a lipase inhibitor of the crude intestinal extract of larvae of Rhynchophorus palmarum, an important agricultural plague, showing potential for control of this pest. Within this context, the real potential of this biotechnological application deserves further studies.
• Design, synthesis, and evaluation of guanylhydrazones as potential inhibitors or reactivators of acetylcholinesterase
  作者：Elaine da Conceição Petronilho、Magdalena do Nascimento Rennó、Newton Gonçalves Castro、Fernanda Motta R. da Silva、Angelo da Cunha Pinto、José Daniel Figueroa-Villar

  DOI：10.3109/14756366.2015.1094468

  日期：2016.11.1

  Analogs of pralidoxime, which is a commercial antidote for intoxication from neurotoxic organophosphorus compounds, were designed, synthesized, characterized, and tested as potential inhibitors or reactivators of acetylcholinesterase (AChE) using the Ellman's test, nuclear magnetic resonance, and molecular modeling. These analogs include 1-methylpyridine-2-carboxaldehyde hydrazone, 1-methylpyridine-2-carboxaldehyde guanylhydrazone, and six other guanylhydrazones obtained from different benzaldehydes. The results indicate that all compounds are weak AChE reactivators but relatively good AChE inhibitors. The most effective AChE inhibitor discovered was the guanylhydrazone derived from 2,4-dinitrobenzaldehyde and was compared with tacrine, displaying similar activity to this reference material. These results indicate that guanylhydrazones as well as future similar derivatives may function as drugs for the treatment of Alzheimer's disease.
• Improving the inhibitory activity of arylidenaminoguanidine compounds at the N-methyl-d-aspartate receptor complex from a recursive computational-experimental structure–activity relationship study
  作者：Joshua R. Ring、Fang Zheng、Aaron J. Haubner、John M. Littleton、Peter A. Crooks

  DOI：10.1016/j.bmc.2013.01.051

  日期：2013.4

  Using a combination of both the partial least squares (PLS) and back-propagation artificial neural network (ANN) pattern recognition methods, several models have been developed to predict the activity of a series of arylidenaminoguanidine analogs as inhibitory modulators of the N-methyl-D-aspartate receptor complex. This was done by correlating structural and physicochemical descriptors obtained from computation software with the experimentally observed [H-3]MK-801 displacement ability of a small library of synthesized and in vitro screened arylidenaminoguanidines. Results for the generated PLS model were r(2) = 0.814, rmsd = 0.208, r(CV)(2) = 0.714, loormsd = 0.261. The ANN model was created utilizing the eleven descriptors from the PLS model for comparison. The quality of the ANN model (r(2)=0.828, rmsd = 0.200, r(CV)(2) = 0.721, loormsd = 0.257) is similar to the PLS model, and indicates that the feature between the inputs and the output is majorly linear. These computational models were able to predict inhibition of the NMDA receptor complex by this series of compounds in silico, affording a predictive structure-based 'pre-screening' paradigm for the arylideneaminoguanidine analogs. (C) 2013 Elsevier Ltd. All rights reserved.