European Journal of Chemistry 2011, 2(1), 65-69 | doi: https://doi.org/10.5155/eurjchem.2.1.65-69.303 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Synthesis and antifungal activity of some new pyrido[2,3-d]pyrimidines


Fatin Ismail Hanafy (1,*)

(1) Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, EG-11711, Egypt
(*) Corresponding Author

Received: 05 Nov 2010 | Revised: 01 Feb 2011 | Accepted: 22 Dec 2010 | Published: 28 Mar 2011 | Issue Date: March 2011

Abstract


Some new pyrido[2,3-d]pyrimidine derivatives (3a-c) were synthesized from 2-amino-5-cyano-6-methoxy-4-(4-methoxyphenyl)pyridine-3-carboxamide. 7-methoxy-5-(4-methoxy phenyl)-4-oxo-2-phenyl-3,4-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (3b) and 7-met-hoxy-5-(4-methoxyphenyl)-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (3c) are used in synthesizing 7a,b, then 8a,b. 7-methoxy-5-(4-methoxyphenyl)-2-methyl-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (3a) and 4-hydrazinyl-7-methoxy-5-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine-6-carbonitrile (8b) were condensed with different carbonyl compounds to produce compounds 4, 5, 6 and 9, 10, 11, 12. 3-Methoxy-1-(4-methoxyphenyl)-6-phenyl-7-hydropyridino[2,3-d]1,2,3,4-tetrazolo[1,5-e]pyrimidine-2-carbo-nitrile (13) was synthesized from 8a or 7a. Condensation of 8b with acetophenone to yield 14, which on further reaction gave 15 then 16. 4-Hydrazinyl-7-methoxy-5-(4-methoxyphenyl)-2-phenylpyrido[2,3-d]pyrimidine-6-carbonitrile (8a) also condensed with 4-amino antipyrine giving 17 then 18. Structures of these compounds have been deduced upon the basis of elemental analysis and spectral data. Significant antifungal activities were observed for some of the synthesized compounds.

2_1_65_69_800


Keywords


Pyrido[2,3-d]pyrimidine; Fusion; Condensation; Active methyl group; Oxidative cyclization; Antifungal activity

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.2.1.65-69.303

Links for Article


| | | | | | |

| | | | | | |

| | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1646 times | icon graph PDF Article downloaded 590 times


Citations

/


[1]. Yasser H. Zaki, Sobhi M. Gomha, Amany M. G. Mohamed
Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents
Chemistry Central Journal  11(1), , 2017
DOI: 10.1186/s13065-017-0286-0
/


[2]. A. Thomann, J. Zapp, M. Hutter, M. Empting, R. W. Hartmann
Steering the azido–tetrazole equilibrium of 4-azidopyrimidines via substituent variation – implications for drug design and azide–alkyne cycloadditions
Organic & Biomolecular Chemistry  13(43), 10620, 2015
DOI: 10.1039/C5OB01006C
/


[3]. Samir Kamel Elsaedany, Mohamed AbdEllatif Zein, Elsayed Mohmoud AbedelRehim, Reda Mohammed Keshk
Synthesis, Anti-Microbial, and Cytotoxic Activities Evaluation of Some New Pyrido[2,3-d]Pyrimidines
Journal of Heterocyclic Chemistry  53(5), 1534, 2016
DOI: 10.1002/jhet.2460
/


[4]. Muniyappapillai Jeganathan Shanmugam, Thangamuthu Mohan Das
A concise pathway to synthesize a novel class of pyrido(2,3-d)pyrimidine-C-β-d-glycosides
Carbohydrate Research  368, 40, 2013
DOI: 10.1016/j.carres.2012.11.013
/


[5]. Ghodsi Mohammadi Ziarani, Sakineh Faramarzi, Negar Lashgari, Alireza Badiei
A simple and clean method for multicomponent synthesis of spiro [indole-tetrahydropyrano(2,3-d)pyrimidine] derivatives using SBA-Pr-SO3H as catalyst under solvent-free conditions
Journal of the Iranian Chemical Society  11(3), 701, 2014
DOI: 10.1007/s13738-013-0342-1
/


[6]. Sherif M. H. Sanad, Ahmed A. M. Ahmed, Ahmed E. M. Mekky
Efficient synthesis and molecular docking of novel antibacterial pyrimidines and their related fused heterocyclic derivatives
Journal of Heterocyclic Chemistry  57(2), 590, 2020
DOI: 10.1002/jhet.3789
/


[7]. Ranin Kawtharani, Khalil Cherry, Mirvat Elmasri, Mohamed Abarbri
An Easy Access to 4‐Trifluoromethylated 7‐(4‐Substitued‐1 H ‐1,2,3‐Triazol‐1‐yl)Pyrimido[1,2‐ b ]Pyridazin‐2‐One Systems
ChemistrySelect  4(38), 11222, 2019
DOI: 10.1002/slct.201902375
/


[8]. Rachel L. Beingessner, Yiwen Fan, Hicham Fenniri
Molecular and supramolecular chemistry of rosette nanotubes
RSC Advances  6(79), 75820, 2016
DOI: 10.1039/C6RA16315G
/


[9]. R. G. Melik-Ohanjanyan, T. R. Hovsepyan, G. S. Karakhanyan, S. G. Israelyan, L. E. Nersesyan, G. A. Panosyan
One-Step Three-Component Synthesis of New 2,5,6,7-Functionalized 5,8-Dihydropyrido-[2,3-d]pyrimidin-4(3H)-ones
Russian Journal of Organic Chemistry  54(1), 107, 2018
DOI: 10.1134/S1070428018010104
/


[10]. Mallu Lavanya, Indira Viswambaran Asharani, Dhakshanamurthy Thirumalai
One pot multi‐component synthesis of functionalized spiropyridine and pyrido[2,3‐d]pyrimidine scaffolds and their potent in‐vitro anti‐inflammatory and anti‐oxidant investigations
Chemical Biology & Drug Design  93(4), 464, 2019
DOI: 10.1111/cbdd.13434
/


[11]. Y. U. Shmoylova, Yu. A. Kovygin, D. Yu. Vandyshev, I. V. Ledenyova, E. A. Kosheleva, Kh. S. Shikhaliev
Efficient Synthesis of Pyrido[2,3-d]pyrimidines by Recyclization of N-Arylitaconimides with Aminopyrimidinones
Russian Journal of Organic Chemistry  56(9), 1512, 2020
DOI: 10.1134/S107042802009002X
/


References


[1]. Burova, O. A.; Bystrykova, I. D.; Smirnova, N. M.; Safonova, T. S. Chem. Heterocyc. Comp. 1991, 27, 394-398.
doi:10.1007/BF00480837

[2]. Rahman, L. K. A.; Chhabra, S. R. Med. Res. Rev. 1988, 8, 95-155.
doi:10.1002/med.2610080106
PMid:3278183

[3]. Gangjee, A.; Vasudevan, A.; Queener, F.; Kisliuk, R. J. Med. Chem. 1996, 39, 1438-1446.
doi:10.1021/jm950786p
PMid:8691474

[4]. Zink, M.; Lanig, H.; Troschutz, R. Eur. J. Med. Chem. 2004, 39, 1079-1088.
doi:10.1016/j.ejmech.2004.09.001
PMid:15571870

[5]. Cordeu, L.; Cubedo, E.; Bandres, E.; Rebollo, A.; Saenz, X.; Chozas, H.; Dominguez, M.; Echeverria, M.; Mendivil, B.; Sanmartin, C.; Palop, J.; Font, M.; Foncillas, J. Bioorg. Med. Chem. 2007, 15, 1659-1669.
doi:10.1016/j.bmc.2006.12.010

[6]. Monge, A.; Martinez, V.; San Martin, C.; Simon, M. A. Spanish Patent ES 1994 2, 056, 742. [Chem. Abstr. 1995, 122, 105912q].

[7]. Parmar, K.; Suthar, B.; Suthar, A.; Maheta, A. J. Heterocycl. Chem. 2009, 46, 975-679.
doi:10.1002/jhet.190

[8]. Koeckkritz, P.; Ruhmann, C.; Fieblinger, D.; Schroeder, C.; Joksch, B.; Heider, B.; Weiher, B. Liebscher J. Ger. Offen. DE 4, 117, 802 [Chem. Abstr. 1993, 118, 191550s].

[9]. Narayana, B.; Ram Rao, A.; Shanthan Rao, P. Eur. J. Med. Chem. 2009, 44, 1369-1376.
doi:10.1016/j.ejmech.2008.05.025
PMid:18603332

[10]. Kanth, S.; Reddy, G.; Kishore, K.; Shanthan Rao, P.; Narsaiah, B.; Murthy, U. Eur. J. Med. Chem. 2006, 41, 1011-1016.
doi:10.1016/j.ejmech.2006.03.028
PMid:16766088

[11]. El-Subbagh, H. I.; Abuzaid, S. M.; Mahran, M. A.; Badria, F. A.; Al-Obaid, A. M. J. Med. Chem. 2000, 43, 2915-2921.
doi:10.1021/jm000038m
PMid:10956199

[12]. Ashalatha, B. V.; Narayana, B.; Vijaya Raj, K. K.; Suchetha Kumari, N. Eur. J. Med. Chem. 2007, 42, 719-728.
doi:10.1016/j.ejmech.2006.11.007
PMid:17189665

[13]. Seada, M.; El-Behairy, M. A.; Jahine, H.; Hanafy, F. Orient. J. Chem. 1989, 5, 273-280.

[14]. Chan, J.; Gustin, D.; Divirgilio, E. S.; Guram, A.; Faul, M. M. Synthesis 2007, 23, 3678-3682.
doi:10.1055/s-2007-990878

[15]. Seada, M.; Abdel-Rahman, R. M.; El-Behairy, M.; Hanafy, F. Asian J. Chem. 1992, 4, 604-614.

[16]. Okafor, C. O. J. Org. Chem. 1973, 38, 4386-4390.
doi:10.1021/jo00965a008

[17]. Dehuri, S. N.; Pradhan, P. C.; Nayak, A. J. Indian Chem. Soc. 1983, 60, 475-481.

[18]. Seada, M.; Abdel-Rahman, R. M.; Hanafy, F. J. Indian Chem. Soc. 1992, 69, 882-884.

[19]. Khan, K. M.; Saify, Z. S.; Zeesha, A. K.; Ahmed, M.; Saeed, M.; Schick, M.; Bkohlbau, H. J.; Voelter, W. Arzneim-Forsch. 2000, 50, 915-922.
PMid:11105234

[20]. Rahman, A. U.; Choudhary, M. I.; Thomsen, W. J. “Bioassay Techniques for drug development, 16 the Netherlands”: Harwood Academic Publishers 2001.
doi:10.4324/9780203304532

[21]. Jorgensen, J. H.; Crawford, S. A.; Mc Elmeel, M. L.; Fiebelkorn, K. R. J. Clin. Microbiol. 2004, 42, 1800-1802.
doi:10.1128/JCM.42.4.1800-1802.2004
PMid:15071055 PMCid:387617


How to cite


Hanafy, F. Eur. J. Chem. 2011, 2(1), 65-69. doi:10.5155/eurjchem.2.1.65-69.303
Hanafy, F. Synthesis and antifungal activity of some new pyrido[2,3-d]pyrimidines. Eur. J. Chem. 2011, 2(1), 65-69. doi:10.5155/eurjchem.2.1.65-69.303
Hanafy, F. (2011). Synthesis and antifungal activity of some new pyrido[2,3-d]pyrimidines. European Journal of Chemistry, 2(1), 65-69. doi:10.5155/eurjchem.2.1.65-69.303
Hanafy, Fatin. "Synthesis and antifungal activity of some new pyrido[2,3-d]pyrimidines." European Journal of Chemistry [Online], 2.1 (2011): 65-69. Web. 25 Feb. 2021
Hanafy, Fatin. "Synthesis and antifungal activity of some new pyrido[2,3-d]pyrimidines" European Journal of Chemistry [Online], Volume 2 Number 1 (28 March 2011)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.2.1.65-69.303

CrossRef | Scilit | GrowKudos | Researchgate | Publons | Microsoft | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2011, 2(1), 65-69 | doi: https://doi.org/10.5155/eurjchem.2.1.65-69.303 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2021  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2021 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.