Modern Organic Chemistry Research

Download PDF (552.7 KB) PP. 10 - 17 Pub. Date: August 8, 2020

DOI: 10.22606/mocr.2020.51002

• Hussniya A. Al-Difar
  Chemistry Department, Science Faculty, University of Benghazi, Benghazi, Libya
• Khalid M. Darwish^*
  Chemistry Department, Science Faculty, University of Benghazi, Benghazi, Libya
• Amera AL-Hijazy
  Chemistry Department, Science Faculty, University of Benghazi, Benghazi, Libya
• Noor EL-Barassi
  Chemistry Department, Science Faculty, University of Benghazi, Benghazi, Libya
• Haneen Al-Difar
  Chemistry Department, Science Faculty, University of Benghazi, Benghazi, Libya

In preparations of some coumarin derivatives, salicylaldehyde was reacted with ethyl acetoacetate in a catalytic amount of piperidine to produce 3-acetylcoumarin 3 through a reaction like Pechmann condensation. The product was then condensed with aromatic aldehydes to produce coumarinyl derivatives as chalcones 5a-b. These, in turn, were reacted with o-phenylene diamine to obtain the corresponding diazepines 7a-b. On the other hand, the synthesized products were examined for their antibacterial activity. Structures of the synthesized products were confirmed with the help of their melting points, TLC analysis and spectral data.

Salicylaldehyde, 3-Acetyl coumarin, OPDA

[1] Batra Nikhil, Batra Shikha, Pareek Anil, Nagori Badri Prakash. (2012), "Diverse pharmacological activities of 3- substituted coumarins: A review", Int. Res. Journal of Pharm, vol. 3(7), pp. 24-29.

[2] Sengupta AK, Sen S, Srivastava V. (1989), "Synthesis of Coumarin Derivatives as Possible Antifungal and Antibacterial Agents." J. Indian Chem. Soc., vol. 66, pp. 710-716.

[3] R Sastry Shridhar, Reddy CV, Vaidya NK, Moorty SR, Reddy GS, Thapar GS, et al. (1978), "Antimicrobial agents: Synthesis and antibacterial activity of some new 4-[2-( heteroaryl) vinyl] coumarins," Indian J. Chem, vol. 16B, pp. 704-708.

[4] Gadaginmath, S Guru, Joshi, G Raghvendra, et al. (1995), "Synthesis and antimicrobial activity of benzimidazolyl / coumarinylmethoxyindoles," Indian J. Chem, vol. 34B: 120-124.

[5] Koneni V Sashidhara, Kumar Abdhesh, Kumar Manoj, Sarkar Jayanta B and Sinha Sudhir (2010), "Synthesis and in vitro evaluation of novel coumarinchalcone hybrids as potential Anticancer agents," Bioorganic and Medicinal Chemistry Letters, vol. 20 (24), pp. 7205‐7211.

[6] Olayinka O Ajania and Obinna C Nwinyi (2010), "Microwave-Assisted Synthesis and Evaluation of Antimicrobial Activity of 3-{3-(s-Aryl and s-Heteroaromatic) acryloyl}-2Hchromen-2-one Derivatives," J. Heterocyclic Chem, vol. 47, pp. 179-187.

[7] Gummudavelly Sandeep, Y Sri Ranganath, S Bhasker and N Rajkumar (2009), "Synthesis and Biological Screening of Some Novel Coumarin Derivatives," Asian J. Research Chem, vol. 2(1). pp. 46-48.

[8] Mulwad VV and Shirodkhar JM. (2002), "Synthesis of some of the antibacterial compounds from 4- hydroxycoumarins: Part II," Indian Journal of Chemistry, vol. 41B, pp. 1263-1267.

[9] Raviraj K, Manjunath G, Manohar K. (2004), "Synthesis and biological activities of some substituted 4-{4-(1,5- Diphenyl-1H-pyrazol-3 yl) phenoxymethyl} coumarins," Indian J Chem, vol. 13, pp. 201-204.

[10] Rao Rajeshwar V, Srimanth K and Kumar Vijaya P. (2004), "Synthesis of 3-[3- substituted thio]-7H-1,2,4- triazolo [3,4-b] [1,3,4]thiadiazin-6-yl]-2H-1-benzopyran-2-ones and 3-[3-amino aryl/heterocyclyl]-7H-1,2,4- triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-2H-1-benzopyran-2-ones," Indian Journal of Heterocyclic chemistry, vol. 14, pp. 141-144.

[11] Sadhu, S.K.; Okuyama, E.; Fujimoto, H.; Ishibashi, M. (2003), "Separation of Leucas Aspera, a Medicinal Plant of Bangladesh, Guided by Prostaglandin Inhibitory and Antioxidant Activities," Chem. Pharm. Bull., vol. 51, pp. 595–598.

[12] Mohamed N Ibrahim, Hussniya-Al-Difar (2013), "synthesis and biological activity study of some heterocyclic’s derived from dibenzalacetone," Ijesm Journal, vol. 2 (3), pp. 1-7.

[13] Seranthimata Samshuddin, Badiadka Narayana, Balladka Kunhanna sarojini Hemmigs. Yathirajan and Ramappa Raghavendra (2012), "Synthesis, characterization and biological evaluation of functionalized derivatives of versatile synthon 4, 4’-difluoro chalcone," Der pharma chemical, vol. 4(4), pp. 1445-1457.

[14] Ali Irfan, Laila Rubab, Mishbah Ur Rehman, Rukhsana Anjum, Sami Ullah, Mahwish Marjana, Saba Qadeer and Sadia Sana (2020), "Coumarin sulfonamide derivatives: An emerging class of therapeutic agents," Heterocycl. Commun., vol. 26, pp. 46–59.

[15] Irena Kostova, Jan Mojzis. (2007), "Biologically active coumarins as inhibitors of HIV-1," Future HIV Ther., vol. 1(3), pp. 315–329.

[16] Gnerre C, Catto M, Leonetti F, Weber P, Carrupt PA, Altomare C, et al. (2000), "Inhibition of monoamine oxidases by functionalized coumarin derivatives: biological activities, QSARs, and 3D-QSARs," J Med Chem., vol. 43, pp. 4747–58.

[17] Musiliyu A. Musa, M. Omar F. Khan, and John S. Cooperwood (2009), "Synthesis and antiproliferative activity of coumarin-estrogen conjugates against breast cancer cell lines," Lett Drug Des Discov., vol. 6(2), pp. 133–138.