European Journal of Chemistry

Crystal structure of 6-amino-3-methyl-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

Crossmark


Main Article Content

Naresh Sharma
Indrajit Karmakar
Goutam Brahmachari
Vivek Kumar Gupta

Abstract

The crystal structure of the title compound, 6-amino-3-methyl-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile, were determined by single crystal X-ray structure analysis. The compound C14H12N4O crystallizes in the triclinic crystal system with the P-1 space group (no. 2), having unit cell parameters a = 6.4788(7) Å, b = 8.8433(7) Å, c = 10.7377(9) Å, α = 103.456(7)°, β = 99.207(8)°, γ = 92.451(8)°, = 588.55(9) Å3, Z = 2. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at room temperature and refined by full-matrix least-squares procedure with a final R-value of 0.0464 for 1432 observed reflections. The dihedral angle between the pyran ring and the pyrazole ring is 178.08(6)°, between the pyrazole ring and the benzene ring is 98.92(6)° and between the pyran ring and the benzene ring is 97.10(5)°. The molecules in the crystal are linked to an infinite two-dimensional network by N−H···N and C−H···π types of hydrogen bonds. Molecules are also reinforced by the π···π interaction between the pyrazole ring and the pyran ring, respectively.


icon graph This Abstract was viewed 110 times | icon graph Article PDF downloaded 38 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
Sharma, N.; Karmakar, I.; Brahmachari, G.; Gupta, V. K. Crystal Structure of 6-Amino-3-Methyl-4-Phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-Carbonitrile. Eur. J. Chem. 2024, 15, 143-148.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Nasr, M. N.; Gineinah, M. M. Pyrido [2, 3-d]pyrimidines and Pyrimido[5′, 4′:5, 6]pyrido[2, 3-d]pyrimidines as New Antiviral Agents: Synthesis and Biological Activity. Arch. Pharm. (Weinheim) 2002, 335, 289-295.
https://doi.org/10.1002/1521-4184(200208)335:6<289::AID-ARDP289>3.0.CO;2-Z

[2]. Ismail, Z. H., Aly, G. M.; El-Degwi, M. S.; Heiba, H. I.; Ghorab, M. M. Synthesis and insecticidal activity of some new pyranopyrazoles, pyrazolopyranopyrimidines, and pyrazolopyranopyridines. Egypt. J. Biotechnol. 2003, 13, 73-82.

[3]. Abdelrazek, F. M.; Metz, P.; Metwally, N. H.; El-Mahrouky, S. F. Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3-c]pyrazole derivatives. Arch. Pharm. (Weinheim) 2006, 339, 456-460.
https://doi.org/10.1002/ardp.200600057

[4]. Ali, T. E.; Assiri, M. A.; El-Shaaer, H. M.; Abdel-Kariem, S. M.; Abdel-Monem, W. R.; El-Edfawy, S. M.; Hassanin, N. M.; Shati, A. A.; Alfaifi, M. Y.; Elbehairi, S. E. I. Synthesis and in vitro antimicrobial, antioxidant, and antiproliferative activities of some new pyrano[2,3-c]pyrazoles containing 1,2-azaphospholes, 1,3,2-diazaphosphinines and phosphonate moieties. Synth. Commun. 2021, 51, 2478-2497.
https://doi.org/10.1080/00397911.2021.1939059

[5]. Kuo, S. C.; Huang, L. J.; Nakamura, H. Studies on heterocyclic compounds. 6. Synthesis and analgesic and antiinflammatory activities of 3,4-dimethylpyrano[2,3-c]pyrazol-6-one derivatives. J. Med. Chem. 1984, 27, 539-544.
https://doi.org/10.1021/jm00370a020

[6]. Turan-Zitouni, G. Synthesis of some thiazolyl-pyrazoline derivatives and preliminary investigation of their hypotensive activity. Eur. J. Med. Chem. 2000, 35, 635-641.
https://doi.org/10.1016/S0223-5234(00)00152-5

[7]. Wang, J.-L.; Liu, D.; Zhang, Z.-J.; Shan, S.; Han, X.; Srinivasula, S. M.; Croce, C. M.; Alnemri, E. S.; Huang, Z. Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc. Natl. Acad. Sci. U. S. A. 2000, 97, 7124-7129.
https://doi.org/10.1073/pnas.97.13.7124

[8]. Mohamed, N. R.; Khaireldin, N. Y.; Fahmy, A. F.; El-Sayed, A. A. Facile synthesis of fused nitrogen containing heterocycles as anticancer agents. Der Pharma Chemica 2010, 2(1), 400-417 https://www.derpharmachemica.com/abstract/facile-synthesis-of-fused-nitrogen-containing-heterocycles-as-anticancer-agents-3518.html.

[9]. Bhavanarushi, S.; Kanakaiah, V.; Yakaiah, E.; Saddanapu, V.; Addlagatta, A.; Rani, J. V. Synthesis, cytotoxic, and DNA binding studies of novel fluorinated condensed pyrano pyrazoles. Med. Chem. Res. 2013, 22, 2446-2454.
https://doi.org/10.1007/s00044-012-0239-z

[10]. Zaki, M. E. A.; Soliman, H. A.; Hiekal, O. A.; Rashad, A. E. Pyrazolopyranopyrimidines as a class of anti-inflammatory agents. Z. Naturforsch. C 2006, 61, 1-5.
https://doi.org/10.1515/znc-2006-1-201

[11]. Mandour, A.; El-Sawy, E.; Ebaid, M.; Hassan, S. Synthesis and potential biological activity of some novel 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles and 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles. Acta Pharm. 2012, 62, 15-30.
https://doi.org/10.2478/v10007-012-0007-0

[12]. Hogale, M. B.; Pawar, B. N. Synthesis and biological-activity of L-aroyl-5-(para-sulphamylphenylazo)-3, 4-dimethyl-pyrano [2, 3-c] pyrazol-6 (1H)-ones. J. Indian Chem. Soc., 1989, 66, 206-207.
https://doi.org/10.1002/chin.199004162

[13]. El-Tamany, E. H.; El-Shahed, F. A.; Mohamed, B. H. Synthesis and biological activity of some pyrazole derivatives. J. Serb. Chem. Soc 1999, 64 (1), 9-18.

[14]. Kassem, E. M.; El-Sawy, E. R.; Abd-Alla, H. I.; Mandour, A. H.; Abdel-Mogeed, D.; El-Safty, M. M. Synthesis of certain new fused pyranopyrazole and pyranoimidazole incorporated into 8-hydroxyquinoline through a sulfonyl bridge at position 5 with evaluation of their in-vitro antimicrobial and antiviral activities. Egypt. Pharm. J. 2012, 11, 116.

[15]. Kasiotis, K. M.; Tzanetou, E. N.; Haroutounian, S. A. Pyrazoles as potential anti-angiogenesis agents: a contemporary overview. Front. Chem. 2014, 2, https://doi.org/10.3389/fchem.2014.00078.
https://doi.org/10.3389/fchem.2014.00078

[16]. Foloppe, N.; Fisher, L. M.; Howes, R.; Potter, A.; Robertson, A. G. S.; Surgenor, A. E. Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening. Bioorg. Med. Chem. 2006, 14, 4792-4802.
https://doi.org/10.1016/j.bmc.2006.03.021

[17]. El-Ansary, A. K. E.-D.; Taher, A. T.; El-Rahmany, A. A. E.-H.; El Awdan, S. Synthesis, anti-inflammatory, analgesic and antipyretic activities of novel pyrano[2,3-c]pyrazoles and related fused ring derivatives. Journal of American Science 2014, 10(10), 284-294 https://www.jofamericanscience.org/journals/am-sci/am1010/041_27380am101014_284_294.pdf.

[18]. Abdelrazek, F. M.; Metz, P.; Kataeva, O.; Jäger, A.; El-Mahrouky, S. F. Synthesis and molluscicidal activity of new chromene and pyrano[2,3‐c]pyrazole derivatives. Arch. Pharm. (Weinheim) 2007, 340, 543-548.
https://doi.org/10.1002/ardp.200700157

[19]. Brahmachari, G.; Banerjee, B. Facile and chemically sustainable one‐pot synthesis of a wide array of fused O‐ and N‐heterocycles catalyzed by trisodium citrate dihydrate under ambient conditions. Asian J. Org. Chem. 2016, 5, 271-286.
https://doi.org/10.1002/ajoc.201500465

[20]. Bihani, M.; Bora, P. P.; Bez, G.; Askari, H. Amberlyst A21 catalyzed chromatography-free method for multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles in ethanol. ACS Sustain. Chem. Eng. 2013, 1, 440-447.
https://doi.org/10.1021/sc300173z

[21]. Sheldrick, G. M., SHELXS-97 and SHELXL-97, Program for Crystal Structure Solution and Refinement, University of Gottingen, Gottingen, 1997.

[22]. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds. J. Chem. Soc., Perkin Trans. 2 1987, S1.
https://doi.org/10.1039/p298700000s1

[23]. Low, J. N.; Cobo, J.; Portilla, J.; Quiroga, J.; Glidewell, C. Bis(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3,4,5-trimethoxyphenylmethane: sheets built from N-H...N and N-H...O hydrogen bonds. Acta Crystallogr. Sect. E Struct. Rep. Online 2004, 60, o1034-o1037.
https://doi.org/10.1107/S1600536804011511

[24]. Topno, N. S.; Kumaravel, K.; Kannan, M.; Vasuki, G.; Krishna, R. 6-Amino-3,4-dimethyl-4-phenyl-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile. Acta Crystallogr. Sect. E Struct. Rep. Online 2011, 67, o956-o956.
https://doi.org/10.1107/S1600536811009354

[25]. Sharma, N.; Brahmachari, G.; Banerjee, B.; Kant, R.; Gupta, V. K. Ethyl 6-amino-5-cyano-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate dimethyl sulfoxide monosolvate. Acta Crystallogr. Sect. E Struct. Rep. Online 2014, 70, o795-o796.
https://doi.org/10.1107/S1600536814013270

[26]. Sharma, N.; Brahmachari, G.; Banerjee, B.; Kant, R.; Gupta, V. K. 6-Amino-3-methyl-4-(3,4,5-trimethoxyphenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile. Acta Crystallogr. Sect. E Struct. Rep. Online 2014, 70, o875-o876.
https://doi.org/10.1107/S1600536814015670

[27]. Mohamed, S. K.; Akkurt, M.; Abdelhamid, A. A.; Singh, K.; Allahverdiyev, M. A. 2-Amino-4-(4-chlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile. Acta Crystallogr. Sect. E Struct. Rep. Online 2012, 68, o1414-o1415.
https://doi.org/10.1107/S1600536812015838

[28]. Etter, M. C.; MacDonald, J. C.; Bernstein, J. Graph-set analysis of hydrogen-bond patterns in organic crystals. Acta Crystallogr. B 1990, 46, 256-262.
https://doi.org/10.1107/S0108768189012929

[29]. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Patterns in hydrogen bonding: Functionality and graph set analysis in crystals. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573.
https://doi.org/10.1002/anie.199515551

[30]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339-341.
https://doi.org/10.1107/S0021889808042726

Supporting Agencies

University of Jammu, Jammu Tawi-180006, India
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms
Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).