Department of Pharmaceutical Chemistry, Shivlingeshwar college of pharmacy Almala, 413520, Maharashtra, India
Department of Pharm D, Vikas Institute of pharmaceutical sciences Rajamahendravaram,533103, Andhra Pradesh, India
A, B-unsaturated carbonyl compounds are organic molecules that share enones and enals' general structure. They are adaptable molecules with a diverse array of biological functions. One significant class of naturally occurring bioactive substances are flavonoids. Chalcones are a significant class of flavonoids that can be made using the claisen process. Their biological functions and industrial applications are diverse. They are produced synthetically by claisen schmidt condensation, which permits the cross-aldol condensation of suitable aldehydes and ketones by an acid- or alkaline-catalyzed reaction that subsequently permits dehydration. As a result, it is thought to be worthwhile to conduct a comparative study using conventional and microwave assisted synthesis (by applying green chemis try) to carry out biological activity like (antimicrobial and antifungal activity). The research study has been conducted as result the microwave assisted synthesis was found to be superior over convectional method and after performing anti-microbial and anti-fungal activities few of the group have showed good activities as a result further studies is required.
Diaryl propinones are widely distributed in nature and originate from the ferns of higher plants. These are compounds with an unsaturated side chain that are aromatic. It has been determined that the diaryl propinones have anti-bacterial, anti-fungal, and insecticidal characteristics since they have been documented to have analgesic, anti-inflammatory, and anti-pyretic qualities. Likewise, possess qualities that are anti-hypertensive, anti-diabetic, and antioxidant. the diaryl propinones, which have three carbon ?, ?-unsaturated carbonyl systems connecting two or more aromatic rings. They are discovered to be naturally occurring in edible plants and serve as building blocks for the synthesis of flavonoids and isoflavonoids. The term "chalcone" was initially used by Kostanecki, who also accomplished grounder aking work in the synthesis of naturally occurring coloring agents. Chalcones are 1,3-diphenyl-2-propene-1-one compounds with three carbons and an unsaturated carbonyl system (?, ?) connecting the aromatic rings. They are thought to be the precursors of flavonoids and isoflavonoids and are found in large quantities in edible plants (Rajendrapr asad et al, 2008), (Chetana B et al, 2009).1,2
Diaryl propinones and their derivatives have been found to be processes of variety of biological and pharmacological activities like Cytotoxic, Anticancer Chemo protective, anti-proliferative, anti-malarial, anti-viral, anti-HIV activities, etc. Chemistry has become more and more popular as a replacement for the standard, conventional method of synthesis because it is renowned for its quick organic synthesis, ease of access to high temperatures, good control over the amount of energy added to the reaction, and higher yields. Some of the newly synthesized derivatives were tested as antiviral agents against HAV. In addition, the cytotoxic activity of Some prepared deriva tives against HepG2 and MCF-7 Cell lines was evaluated (Arshi et al ,2009) ,(Vyas et al,2009) .3,4
Experimental part
General procedure for the synthesis of chalcones by Claisen-Schmidt condensation
Equimolar quantities (0.001mol) of 2-acetylthiophene and respective aldehydes (0.001mol), were mixed and dissolved in minimum amount (3ml) of alcohol, to this aqueous potassium hydroxide solution (30%) was added slowly and mixed occasionally for 24 hrs, at room temperature. Completion of the reaction was identified by observing on precoated TLC plates of Merck. After completion of the reaction, the reaction mixture was poured into crushed ice, if necessary acidified with dil HCl. The solid separated was filtered and dried. It was purified by recrystallization or by column chromatography performed on silica gel (100-200 Mesh, Merck), using ethyl acetate and hexane mixture as mobile phase.5
Equimolar quantities (0.001mol) of 2-acetylthiophene and respective aldehydes (0.001mol) were mixed and dissolved in minimum amount (3ml) of alcohol; to this aqueous potassium hydroxide solution (30%) was added slowly and mixed. The entire reaction mixture was microwave irradiated for about 2-6 minutes at 180 watts, then kept aside for 1-3 hrs. Completion of the reaction was identified by observing on precoated TLC plates of Merck. After completion of the reaction, the reaction mixture was poured into crushed ice, if necessary acidified with dil HCl. The solid separated was filtered and dried. It was purified by recrystallization or by column chromatography performed on silica gel (100-200 mesh, Merck), using ethylacetate and hexane mixture as mobile phase. 6
Table 1. Microwave Method
Table 2. Convectional Method
Molecular weight 229.0689 was found.
1H NMR: 1HNMR spectral data of: 3-(4-methylphenyl)-1-(thiophen-2-yl) prop-2-en-1-one.
(1). IR (cm-1): IR Spectral data of : 3-(4-methylphenyl)-1-(thiophen-2-yl) prop-2-en-1-one.
Anti-Microbial Activity
?-ketoesters are organic compounds that contain a carbonyl group (C=O) attached to a carbon atom that is adjacent to another carbon-carbon double bond (C=C). These compounds have been of interest in the field of medicinal chemistry due to their potential antimicrobial properties. The antimicrobial activity of ?-ketoesters arises from their ability to interact with the microorganisms’ cellular components, such as enzymes or cell membranes, leading to disruption of vital biological processes and ultimately killing or inhibiting the growth of the microorganisms. The synthesis of ?-ketoesters typically involves the condensation reaction between ?-keto acid or ester and an aldehyde or ketone. The resulting compound contains the ?-ketoesters functional group. To assess the antimicrobial activity of synthesized ?-ketoesters, various in vitro and in vivo assays can be performed. These assays involve exposing the target microorganisms, such as Xanthomonas Citri, Ervinia Carotovora, E. coli Proteas vulgerius, to different concentrations of the synthesized compounds and measuring their inhibitory effects on microbial growth. The specific mechanism of antimicrobial action can vary depending on the structure of the alpha ?-ketoesters and the target microorganism. It may involve interference with enzymatic processes, inhibition of cell walls synthesis, disruption of cell membrane integrity, or interference with DNA replication. Experimental studies, including minimum inhibitory concentration (MIC) assays, time-kill kinetics, and zone of inhibition tests, are commonly employed to evaluate the antimicrobial activity of synthesized ?-ketoesters. These studies help determine the effective concentration required to inhibit microbial growth, the rate of microbial killing over time, and the extent of growth inhibition in the vicinity of the compound.11,12,13 ,14.
RESULT AND DISCUSSION
The synthesized ??-unsaturated carbonyl compound (1 to 9) was tested against various gram+ve and gram-ve organisms (Xanthomo nas Citri, Ervinia Carotovora, E. coli Proteas vulgerius) and taken Ciprofloxacin as standard drug for comparison, compound 1,4-methylphenyl derivative of ??-carbonyl compound was found more effective among all compounds. Compound 5 nitro derivative shows goodactivity against ProteaseVulgerius. Compound 7 ethoxy derivatives have shown good activity against Ervinia Carotovora.
CONCLUSION
A comparative study on the synthesis of ??-unsaturated carbonyl compounds and their biological activity provides valuable information on the preparation of these compounds and their potential applications in the field of drug development. In addition, structure–activity relationship (SAR) studies have provided valuable information on key structural features that influence the pharmacological properties of ?-ketoesters. Overall, a comparative study on the synthesis of ??-unsaturated carbonyl compounds and their biological evaluation illuminates the potential applications of these compounds in drug development. The study provides a comprehensive overview of various synthetic methods, but also provides valuable insights into their biological properties and structure-activity relationships. Synthesis of ?, ?-unsaturated carbonyl compounds was carried out by Convectional and Microwave assisted synthesis. The Microwave assisted synthesis is proved to be superior ovesr convectional method because, less consumption of chemicals, good yield in short span of time. The antimicrobial activity was successfully carried out and few compounds have shown good activity and eco-friendly.
ACKNOWLEDGEMENTS
I would like to thank my guide Dr. Md Rayees Ahmad for his valuable guidance and support throughout the research work. The completion of my research work would not have been possible without his support. Also, thanks to Principal, Dharashive V. M. For providing the laboratory facility and his persistent creative encouragement and valuable guidance throughout this research work. It has been a great pleasure and wonderful learning experience to work under his supervision.
REFERENCES:
Shaikh Sabiya, MD Rayees Ahmad, Vishweshwar Dharashive , Dachawar Saiprasad, Shaikh Ghafurunnisa, Wadje Suresh, Sontake Pooja, Tange Pooja, Kolhe Sampada, Bamne Ajay, Ghume Nitin, Green Synthesis And Biological Evaluation Of ?, ? - Unsaturated Carbonyl Compounds By Microwave Irradiation And Conventional Methods, Int. J. of Pharm. Sci., 2024, Vol 2, Issue 4, 26-34. https://doi.org/10.5281/zenodo.10904145
10.5281/zenodo.10904145
