Ram Chandra Reddy Jala

Synthesis of novel ethyl 1-ethyl-6-fluoro-7-(fatty amido)-1,4-dihydro-4-oxoquinoline-3-carboxylate derivatives and their biological evaluation

A series of novel ethyl 1-ethyl-6-fluoro-7-(fatty amido)-1,4-dihydro-4-oxoquinoline-3-carboxylate derivatives were prepared through multistep synthesis. The key step in the synthesis was to obtain the C-7 fatty amide derivative. The azide was selectively formed at C-7 position using sodium azide at 60°C. Subsequently, the azide was reduced under mild conditions using zinc and ammonium chloride to form the corresponding amine. The synthesized derivatives were further subjected to biological evaluation studies like cytotoxicity against a panel of cancer cell lines such as DU145, A549, SKOV3, MCF7 and normal lung cells, IMR-90 as well as with antimicrobial and antioxidant activities. It was observed that the carboxylated quinolone derivatives with hexanoic (8a), octanoic (8b), lauric (8d) and myristic (8e) moieties exhibited promising cytotoxicity against all the tested cancer cell lines. The results also suggested that hexanoic acid-based fatty amide carboxylated quinolone derivative (8a) exhibited promising activity against both bacterial and fungal strains and significant antibacterial activity was observed against Staphylococcus aureus MTCC 96 (MIC value of 3.9μg/mL). The compound 8a also showed excellent anti-biofilm activity against Staphylococcus aureus MTCC 96 and Bacillus subtilis MTCC 121 with MIC values of 2.1 and 4.6μg/mL, respectively.

Synthesis and biological evaluation of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thioglycosides

In the present study, the synthesis of 1, 3, 4-thiadiazole-based thioglycosides were accomplished in good yields with employing a convergent synthetic route. The starting material 5-amino-1, 3, 4-thiadiazole-2-thiol and followed by a series of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thiols (4a-4j) were synthesized with different fatty acid chlorides. The glycosylation of compounds 4a-4j were achieved with trichloroacetimidate methodology. Antimicrobial and cytotoxicity activities of title compounds were evaluated. Among the entire compounds lauric acid and myristic acid derivatives showed good and moderate antimicrobial activity. In case of cytotoxicity results of compounds 8a-8j and 9a-9j, the acetate protected short chain (C6:0, C8:0, C10:0) compounds and the free hydroxyl long chain saturated (C16:0, C18:0) and unsaturated (C18:1, C22:1) compounds exhibited good activity against different cancer cell lines. Further, the free hydroxyl compounds 9a, 9c-9j did not show any toxicity towards normal CHO-K1 cell line whereas acylated compounds 8a-8j exhibited toxicity.

An insight into the biological activities of heterocyclic–fatty acid hybrid molecules

Heterocyclic compounds are the interesting core structures for the development of new bioactive compounds. Fatty acids are derived from renewable raw materials and exhibit various biological activities. Several researchers are amalgamating these two bioactive components to yield bioactive hybrid molecules with some desirable features. Heterocyclic-fatty acid hybrid derivatives are a new class of heterocyclic compounds with a broad range of biological activities and significance in the field of medicinal chemistry. Over the last few years, many research articles emphasized the significance of heterocyclic-fatty acid hybrid derivatives. The present review article focuses the developments in designing and biological evaluation of heterocyclic-fatty acid hybrid molecules.

Designer and Functional Food Lipids in Dietary Regimes: Current Trends and Future Prospects

Abstract Oils and fats contribute to the flavor and organoleptic perception of foods (i.e., mouthfeel, taste, aroma, and odor). They also play a vital role in human nutrition. There is a growing trend towards reducing calorie intake (i.e., fat in the diet) in order to prevent cholesterol-related health issues such as atherosclerosis, obesity, and diabetes. In this regard, designer lipids derived using lipid modification play a significant role in enhancing the functional properties (i.e., the rheological and organoleptic attributes) of foods for their use in nutrition and health. Designer lipids are composed of triglycerides containing long-, medium-, or short-chain fatty acids, and the fat imitates the structure of natural materials (i.e., human milk fat substitutes or cocoa butter equivalents). In addition, partial glycerides, reduced-calorie fats, structured phospholipids, and phenolipids are also discussed in this chapter. The need for better quality functional lipids is increasing attention on the production of tailor-made lipids. The latest developments and the current industrial status of all enzymatically modified, commercially important designer lipids are also described.

Design, synthesis, and cytotoxicity evaluation of threonine-based galactoceramide with aromatic groups and various fatty-acyl side chains

In galactoceramides, presence of fatty-acyl group on amide moiety or phytosphingosine group is some of the important features that influence the cytotoxicity. Continuous efforts are in progress to modify the fatty-acid moiety and phytosphingosine group present on the galactoceramides to enhance the cytotoxic potential of these compounds. Hence, in the present study, threonine-based β-galactoceramide and its derivatives were prepared by modifying the fatty-acyl group on amide moiety with different fatty-acyl moieties and aromatic acids employing trichloroacetimidate methodology. The structurally related threonine-based ceramide part was synthesized in multi-step process using different reagents. The ceramide part was glycosylated with galactose using trichloroacetimidate as donor. Further, all the synthesized compounds were evaluated for in vitro cytotoxicity against three cancer cell lines and one normal cell line and all the compounds exhibited good to moderate cytotoxicity against all the tested cancer cell lines. In aromatic derivatives, the compound 8i exhibited promising activity against MCF7, A549 and HeLa cancer cell lines with IC50 values of 14.08, 14.78, and 16.70 µM, respectively. In fatty-acid derivatives, two compounds exhibited promising activity, i.e., compound 8m against HeLa with IC50 value 16.34 µM and compound 8n against MCF7 with IC50 value 18.05 µM. Based on structure–activity relationship, aromatic acid derivatives exhibited potential activity as compared to fatty-acid derivatives. Further, the influence of some of the key factors such as spacer chain length between aromatic residue and amide functional group, methoxy substituents on aryl group, terminal unsaturation of fatty acid and branching chain effect on the cytotoxicity are discussed.Graphical abstract

Synthesis and biological evaluation of 3,6-dialkylsubstituted-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles

A series of 3,6-dialkyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole (10) analogues were prepared through multistep synthesis and evaluated them for their antimicrobial and cytotoxic activities. Synthesis of target compounds was carried out using undecenoic acid as starting material, which is the renewable product of castor oil. The key step in the synthesis was formation of triazolo [3,4-b][1,3,4]thiadiazole using various free fatty acids in presence of

Rice Bran Lecithin: Compositional, Nutritional, and Functional Characteristics

\hbox {POCl}_{3}

Synthesis of dihydrosterculic acid-based monoglucosyl diacylglycerol and its analogues and their biological evaluation

POCl3. It was observed that the undecenyl based triazolothiadiazole with butyl (6a), hexyl (6b) and lauryl (6f) derivatives exhibited promising antimicrobial activity against the tested strains. Particularly, Compound 6a exhibited the most promising activity with MIC value 3.9