Synthesis and Evaluation of Phenol Derivatives of Sulfonyl Chloride Quinoxaline
Abstract
The objective of the present study was to synthesize some new 7-sulfonate of 2, 3- Diphenyl quinoxaline which are more potential as antibacterial than parent quinoxalines. The present study was synthesis of derivatives of sulfonyl chloride quinoxaline and physicochemical and spectral characterization, in vitro antimicrobial screening against gram positive and gram negative bacteria.The concentration of derivatives used as 200 and 400 microgram initially. When 200 µg concentrations was used R6 shows sensitivity towards S. aureus and R6 shows sensitivity towards gram negative E. coli organism. When 400 µg used then R3, R5, and R6 shows sensitivity in case of gram positive organism. And in case of gram negative organism R5, R6 shows sensitivity.Azithromycin is used as Reference drug and a comparative study was done. As compare to reference drug all derivatives shows less sensitivity than S- Standard and R- quinoxaline derivatives.
Keywords: Diphenyl quinoxaline, QSAR, Quinoxaline, Phenol derivatives
Keywords:
QSAR, Quinoxaline, Diphenyl quinoxaline
Downloads
Download data is not yet available.
References
1. Alavi, S., Mosslemin, M.H., Mohebat, R. et al. Green synthesis of novel quinoxaline sulfonamides with antibacterial activity. Res Chem Intermed 2017; 43:4549–4559.
2. Desai, N. C.; Rajpara, K. M.; Joshi, V. V., Microwave induced synthesis of fluorobenzamides containing thiazole and thiazolidine as promising antimicrobial analogs. J Fluorine Chem 2017; 145(0):102-111.
3. Ganapaty S.et al., Sar Study: Impact of hydrazide hydrazones and sulfonamide side chain on in vitro antimicrobial activity of quinoxaline, Int.J. Pharmacol.Biol. 2008; (2):13-18.
4. Agrawal, O. P.; Organic Chemistry Reactions and Reagents, Goel publishing house, New Delhi, 627-628, 686-715.
5. Gupta R. R., Kumar M., Gupta V. Heterocyclic Chemistry, Springer Publication, 1998; 1:13-14.
6. Joule J. A. and K. Mills, Heterocyclic chemistry, 4th ed, Blackwell publication, 2000 194-198.
7. Ali M. M. et al., Synthesis and antimicrobial activity of some novel quinoxalinone derivative, Molecule 2000; 5:864-873.
8. Rohini RR. M. et al., Synthesis and evaluation of novel benzimidazo [1, 2-c] quinazoline -6 -thione derivRtive, 4, 5, M.Pharm thesis, Rajive Gandhi University, Bangalore, 2002.
9. Vicente E., et al, Synthesis and structure –activity relationship of 3-furyl and 3-thienylquinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives against Plasmodium falciparum,”http://www.usc.es/congresos/ecsoc/11/ECSOC11.htm(accessed November 13,2007).
10. Asuncion Burguete et al., synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1, 4-di-N-oxide quinoxaline-2-yl)-2-propen-1-one derivative, Bioorganic and Medicinal Chemistry Letters 2007; 17:6439-6443.
11. Sandra Piras et al., Quinoxaline Chemistry, Synthesis of Methyl [4-(Substituted 2-quinoxalinyloxy) Phenyl] acetate and evaluation of anticancer activity, IL FARMCO 2004; 59:185-194.
12. Iveta Wiedermannova et al., Synthesis of some arylhydrazones of 2-oxo-6,7,dichloro-1, 2-dihydroquinoxaline carbaldehyde, Acta Universitatis Palackianae Olomucensis Facultas Rerum Naturalium , 2002; 46:771.
13. Darabi HR, Mohandessi S, Aghapoor K, Mohsenzadeh F, A recyclable and highly effective sulfamic acid/MeOH catalytic system for the synthesis of quinoxalines at room temperature, Catalysis Communications 8 2007; 389–392.
14. Dong F, et al, A practical and efficient synthesis of quinoxaline derivatives catalyzed by task-specific ionic liquid, Catalysis Communications 2008; 9:317–320.
15. Bhosale RS, Sarda SR, Ardhapure SS, Jadhav WN, Bhusareb SR, Pawar RP, An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst, Tetrahedron Letters 2005; 46:7183–7186.
16. Dae-Kee Kim, Sun Hee Jung, Ho Soon Lee, Purushottam M. Dewang, Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-b type 1 receptor kinase inhibitors, European Journal of Medicinal Chemistry 2009; 44:568-576.
17. Kumar A, Kumar S, Saxena A, De A, Mozumdar S, Ni-nanoparticles: An efficient catalyst for the synthesis of quinoxalines, Catalysis Communications 2008; 9:778–784.
18. Srinivas C, Naga Sesha C, Pavan Kumar S, Rao VJ, Palaniappan S, “Efficient, convenient and reusable polyaniline-sulfate salt catalyst for the synthesis of quinoxaline derivatives”, Journal of Molecular Catalysis A: Chemical 2007; 265:227–230.
19. Bi Bi Fatemeh Mirjalili, Ali Akbari, Nano-TiO2: An eco-friendly alternative for the synthesis of quinoxalines, Chinese Chemical Letters 22 (2011) 753–756.\Vogel’s Textbook of Practical Organic Chemistry, 1989, 5th ed, International student edition, 119.
20. Jerry March, Advanced Organic Chemistry, 2002, 4th ed, Wiley Publication, 496-497. 20. Antonio Carta et al., Novel synthesis of quinoxaline 1, 4 dioxide with in vitro antimicrobial and anticandida activity, Eur. J. Medicinal chemistry, 2002; 37:355-366.
21. Quinoxaline and related compound with antifungal activity, J. Heterocyclic chemistry 23-1391-1394
22. Andres Jaso. et al., Synthesis of new 2-acetyl & 2-benzoyl quinoxaline 1,4-di-N-oxide derivatives as anti-mycobacterium tuberculosis agents, European journal of medicinal chemistry, 2003; 38:791-80
2. Desai, N. C.; Rajpara, K. M.; Joshi, V. V., Microwave induced synthesis of fluorobenzamides containing thiazole and thiazolidine as promising antimicrobial analogs. J Fluorine Chem 2017; 145(0):102-111.
3. Ganapaty S.et al., Sar Study: Impact of hydrazide hydrazones and sulfonamide side chain on in vitro antimicrobial activity of quinoxaline, Int.J. Pharmacol.Biol. 2008; (2):13-18.
4. Agrawal, O. P.; Organic Chemistry Reactions and Reagents, Goel publishing house, New Delhi, 627-628, 686-715.
5. Gupta R. R., Kumar M., Gupta V. Heterocyclic Chemistry, Springer Publication, 1998; 1:13-14.
6. Joule J. A. and K. Mills, Heterocyclic chemistry, 4th ed, Blackwell publication, 2000 194-198.
7. Ali M. M. et al., Synthesis and antimicrobial activity of some novel quinoxalinone derivative, Molecule 2000; 5:864-873.
8. Rohini RR. M. et al., Synthesis and evaluation of novel benzimidazo [1, 2-c] quinazoline -6 -thione derivRtive, 4, 5, M.Pharm thesis, Rajive Gandhi University, Bangalore, 2002.
9. Vicente E., et al, Synthesis and structure –activity relationship of 3-furyl and 3-thienylquinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives against Plasmodium falciparum,”http://www.usc.es/congresos/ecsoc/11/ECSOC11.htm(accessed November 13,2007).
10. Asuncion Burguete et al., synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1, 4-di-N-oxide quinoxaline-2-yl)-2-propen-1-one derivative, Bioorganic and Medicinal Chemistry Letters 2007; 17:6439-6443.
11. Sandra Piras et al., Quinoxaline Chemistry, Synthesis of Methyl [4-(Substituted 2-quinoxalinyloxy) Phenyl] acetate and evaluation of anticancer activity, IL FARMCO 2004; 59:185-194.
12. Iveta Wiedermannova et al., Synthesis of some arylhydrazones of 2-oxo-6,7,dichloro-1, 2-dihydroquinoxaline carbaldehyde, Acta Universitatis Palackianae Olomucensis Facultas Rerum Naturalium , 2002; 46:771.
13. Darabi HR, Mohandessi S, Aghapoor K, Mohsenzadeh F, A recyclable and highly effective sulfamic acid/MeOH catalytic system for the synthesis of quinoxalines at room temperature, Catalysis Communications 8 2007; 389–392.
14. Dong F, et al, A practical and efficient synthesis of quinoxaline derivatives catalyzed by task-specific ionic liquid, Catalysis Communications 2008; 9:317–320.
15. Bhosale RS, Sarda SR, Ardhapure SS, Jadhav WN, Bhusareb SR, Pawar RP, An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst, Tetrahedron Letters 2005; 46:7183–7186.
16. Dae-Kee Kim, Sun Hee Jung, Ho Soon Lee, Purushottam M. Dewang, Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-b type 1 receptor kinase inhibitors, European Journal of Medicinal Chemistry 2009; 44:568-576.
17. Kumar A, Kumar S, Saxena A, De A, Mozumdar S, Ni-nanoparticles: An efficient catalyst for the synthesis of quinoxalines, Catalysis Communications 2008; 9:778–784.
18. Srinivas C, Naga Sesha C, Pavan Kumar S, Rao VJ, Palaniappan S, “Efficient, convenient and reusable polyaniline-sulfate salt catalyst for the synthesis of quinoxaline derivatives”, Journal of Molecular Catalysis A: Chemical 2007; 265:227–230.
19. Bi Bi Fatemeh Mirjalili, Ali Akbari, Nano-TiO2: An eco-friendly alternative for the synthesis of quinoxalines, Chinese Chemical Letters 22 (2011) 753–756.\Vogel’s Textbook of Practical Organic Chemistry, 1989, 5th ed, International student edition, 119.
20. Jerry March, Advanced Organic Chemistry, 2002, 4th ed, Wiley Publication, 496-497. 20. Antonio Carta et al., Novel synthesis of quinoxaline 1, 4 dioxide with in vitro antimicrobial and anticandida activity, Eur. J. Medicinal chemistry, 2002; 37:355-366.
21. Quinoxaline and related compound with antifungal activity, J. Heterocyclic chemistry 23-1391-1394
22. Andres Jaso. et al., Synthesis of new 2-acetyl & 2-benzoyl quinoxaline 1,4-di-N-oxide derivatives as anti-mycobacterium tuberculosis agents, European journal of medicinal chemistry, 2003; 38:791-80
Statistics
48 Views | 34 Downloads
How to Cite
1.
Goyal R, Sharma M, Ahuja D, Jain A. Synthesis and Evaluation of Phenol Derivatives of Sulfonyl Chloride Quinoxaline. JDDT [Internet]. 30Jul.2019 [cited 6Mar.2021];9(4):774-82. Available from: http://www.jddtonline.info/index.php/jddt/article/view/3016
Section
Research
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License. that allows others to share the work with an acknowledgment of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgment of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).
.