Literature DB >> 31391989

Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chloro-benz-yl)-6-oxo-3-phenyl-1,6-di-hydro-pyridazin-1-yl]acetate.

Fouad El Kalai1, Cemile Baydere2, Said Daoui1, Rafik Saddik3, Necmi Dege2, Khalid Karrouchi4, Noureddine Benchat1.   

Abstract

The title pyridazinone derivative, C21H19ClN2O3, is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41 (13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19 (13)°]. In the crystal, C-H⋯O hydrogen bonds generate dimers with R 2 2(10) and R 2 2(24) ring motifs which are linked by C-H⋯O inter-actions, forming chains extending parallel to the c-axis direction. The inter-molecular inter-actions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most significant contributions to the crystal packing are from H⋯H (44.5%), C⋯H/H⋯C (18.5%), H⋯O/H⋯O (15.6%), Cl⋯H/H⋯Cl (10.6%) and C⋯C (2.8%) contacts.

Entities:  

Keywords:  Hirshfeld surface analysis; crystal structure; pyridazine

Year:  2019        PMID: 31391989      PMCID: PMC6658951          DOI: 10.1107/S2056989019007424

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


  17 in total

1.  Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces.

Authors:  Joshua J McKinnon; Dylan Jayatilaka; Mark A Spackman
Journal:  Chem Commun (Camb)       Date:  2007-10-07       Impact factor: 6.222

2.  Design, synthesis and structure-activity relationship studies of 6-phenyl-4,5-dihydro-3(2H)-pyridazinone derivatives as cardiotonic agents.

Authors:  Teng Wang; Ying Dong; Li-Chen Wang; Bing-Ren Xiang; Zhen Chen; Ling-Bo Qu
Journal:  Arzneimittelforschung       Date:  2008

3.  Synthesis, antibacterial and antifungal activity of some new pyridazinone metal complexes.

Authors:  Mehmet Sönmez; Ismet Berber; Esvet Akbaş
Journal:  Eur J Med Chem       Date:  2005-11-15       Impact factor: 6.514

4.  SAR studies of pyridazinone derivatives as novel glucan synthase inhibitors.

Authors:  Gang Zhou; Pauline C Ting; Robert Aslanian; Jianhua Cao; David W Kim; Rongze Kuang; Joe F Lee; John Schwerdt; Heping Wu; R Jason Herr; Andrew J Zych; Jinhai Yang; Sang Lam; Samuel Wainhaus; Todd A Black; Paul M McNicholas; Yiming Xu; Scott S Walker
Journal:  Bioorg Med Chem Lett       Date:  2011-03-30       Impact factor: 2.823

5.  Synthesis and structure-activity relationship of 5-pyridazin-3-one phenoxypiperidines as potent, selective histamine H(3) receptor inverse agonists.

Authors:  Ming Tao; Lisa D Aimone; John A Gruner; Joanne R Mathiasen; Zeqi Huang; Jacquelyn Lyons; Rita Raddatz; Robert L Hudkins
Journal:  Bioorg Med Chem Lett       Date:  2011-12-04       Impact factor: 2.823

6.  Phosphodiesterase inhibitors. Part 3: Design, synthesis and structure-activity relationships of dual PDE3/4-inhibitory fused bicyclic heteroaromatic-dihydropyridazinones with anti-inflammatory and bronchodilatory activity.

Authors:  Koji Ochiai; Satoshi Takita; Tomohiko Eiraku; Akihiko Kojima; Kazuhiko Iwase; Tetsuya Kishi; Kazunori Fukuchi; Tokutaro Yasue; David R Adams; Robert W Allcock; Zhong Jiang; Yasushi Kohno
Journal:  Bioorg Med Chem       Date:  2012-01-28       Impact factor: 3.641

7.  Triazole incorporated pyridazinones as a new class of antihypertensive agents: design, synthesis and in vivo screening.

Authors:  Anees A Siddiqui; Ravinesh Mishra; Mohammad Shaharyar; Asif Husain; Mohd Rashid; Palash Pal
Journal:  Bioorg Med Chem Lett       Date:  2010-12-10       Impact factor: 2.823

8.  4-Benzyl-6-p-tolyl-pyridazin-3(2H)-one.

Authors:  Ahmad Oubair; Jean-Claude Daran; Rachid Fihi; Lhou Majidi; Mohamed Azrour
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-05-20

9.  Synthesis and analgesic and anti-inflammatory activities 6-substituted-3(2H)-pyridazinone-2-acetyl-2-(p-substituted/nonsubstituted benzal)hydrazone derivatives.

Authors:  Mehtap Gökçe; Semra Utku; Esra Küpeli
Journal:  Eur J Med Chem       Date:  2009-05-09       Impact factor: 6.514

10.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
View more
  1 in total

1.  Synthesis, spectroscopy, crystal structure, TGA/DTA study, DFT and molecular docking investigations of (E)-4-(4-methylbenzyl)-6-styrylpyridazin-3(2H)-one.

Authors:  Fouad El Kalai; Emine Berrin Çınar; Chin-Hung Lai; Said Daoui; Tarik Chelfi; Mustapha Allali; Necmi Dege; Khalid Karrouchi; Noureddine Benchat
Journal:  J Mol Struct       Date:  2020-10-10       Impact factor: 3.196

  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.