BITS Faculty Publications
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Item Steroid-triazole conjugates: A brief overview of synthesis and their application as anticancer agents(Elsevier, 2023-09) Sakhuja, RajeevSteroids are biomolecules that play pivotal roles in various physiological and drug discovery processes. Abundant research has been fuelled towards steroid-heterocycles conjugates over the last few decades as potential therapeutic agents against various diseases especially as anticancer agents. In this context various steroid-triazole conjugates have been synthesized and studied for their anticancer potential against various cancer cell lines. A thorough search of the literatures revealed that a concise review pertaining the present topic is not compiled. Therefore, in thus review we summarize the synthesis, anticancer activity against various cancer cell lines and structure activity relationship (SAR) of various steroid-triazole conjugates. This review can lay down the path towards the development of various steroid-heterocycles conjugates with lesser side effects and profound efficacy.Item Regiodivergent Synthesis of Cinnoline-Fused Indazolones through Pd-Catalyzed Annulation of 1-Arylindazolones with Allenoates(ACS, 2022-01) Sakhuja, RajeevA tender-hearted Pd(II)-catalyzed C–H activation of 1-arylindazolones followed by an oxidative [4 + 2] annulation reaction has been accomplished, engaging allenoates as annulating partners. Using this strategy, two different regioisomeric forms of cinnoline-fused indazolones possessing internal and exocyclic double bonds were synthesized in acetic acid and dioxane, respectively. Mild and aerobic conditions, avoiding the use of any metal–oxidant, highlights the rewards of this oxidative annulation protocol.Item Development of Isatin-Based Schiff Bases Targeting VEGFR-2 Inhibition: Synthesis, Characterization, Antiproliferative Properties, and QSAR Studies(Wiley, 2022-05) Sakhuja, RajeevThree sets of isatin-based Schiff bases were synthesized utilizing the molecular hybridization approach. Some of the synthesized Schiff bases show significant to moderate antiproliferative properties against MCF7 (breast), HCT116 (colon), and PaCa2 (pancreatic) cancer cell lines with potency compared to reference drugs 5-fluorouracil (5-FU) and Sunitinib. Among all, compound 17 f (3-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)-1-((1-(2-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methyl)-5-methylindolin-2-one) exhibits promising antiproliferative properties against the MCF7 cancer cell line with 2.1-fold more potency than Sunitinib. However, among all the synthesized compounds, three (5-methylisatin derivatives) were the most effective against HCT116 in comparison to 5-FU. Compound 17 f exhibited the highest anti-angiogenic effect on the vasculature as it significantly reduced BV from 43 mm to 2 mm in comparison to 5.7 mm for Sunitinib and flow cytometry supports the arrest of the cell cycle at G1/S phases. In addition, compound 17 f also showed high VEGFR-2 inhibition properties against breast cancer cell lines. Robust 2D-QSAR studies supported the biological data.Item Luminescent triazolo-fused pyrido[3,4-b]pyrazines as novel fluorophores(Elsevier, 2024-12) Khungar, Bharti; Sakhuja, RajeevA series of organic fluorophores based on novel [1,2,4]triazolo [4′,3':1,2]pyrido [3,4-b]pyrazine architecture were synthesized by a simple two-step protocol. Synthesized organic fluorophores exhibit blue-to-green fluorescence and their UV absorption and fluorescent emission properties were studied. The photophysical properties of synthesized derivatives were tuned by introducing functionalities of varying electronic nature on the core nucleus. The luminescence maxima of the synthesized compounds are found in the range from 427 nm to 503 nm, and the quantum yields ranging from 0.01 to 0.64 were calculated. Among various synthesized molecules, 3-(4-bromophenyl)-8,9-bis(4-methoxyphenyl)-[1,2,4]triazolo [4′,3':1,2]pyrido [3,4-b]pyrazine showed highest quantum yield (ΦF = 0.64), and was further explored for its solvatochromic, acidochromic, aggregation induced fluorescence studies along with theoretical HOMO-LUMO calculationsItem Synthesis of modified bile acids via palladium-catalyzed C(sp3)–H (hetero)arylation(RSC, 2023-07) Chitkara, Deepak; Sakhuja, RajeevA Pd(II)-catalyzed strategy for the diastereo- and regioselective (hetero)arylation of unactivated C(sp3)–H bonds in bile acids is accomplished with aryl and heteroaryl iodides under solvent-free conditions using the 8-aminoquinoline auxiliary as a directing group. This methodology demonstrated excellent functional group tolerance with respect to aryl/heteroaryl iodides on O-protected N-(quinolin-8-yl)cholyl/deoxycholyl amides to afford β-C(sp3)–H (hetero)arylated products in good-to-excellent yields. Moreover, the 8-aminoquinoline (AQ) auxiliary can easily be removed to obtain modified bile acids.Item Lewis Acid Promoted Synthesis of 2(3H)-Benzofuranones(Wiley, 2007-02-07) Sakhuja, RajeevChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDFItem Novel Fluorinated Spiro [Indole-indazolyl-thiazolidine]-2,4′-diones: Design and Synthesis(Taylor & Francis, 2004-09-07) Sakhuja, RajeevThe reaction of indol-2,3-diones ( 1a–i ) with 5-aminoindazole ( 2 ) has resulted in the formation of hitherto unknown 3-(indazol-5-yl)iminoindol-2-ones ( 3a–i ) in quantitative yields which, on 1,3-dipolar cyclocondensation with mercaptoacetic acid ( 4 ), has afforded a series of new spiro heterocycles, 3′-(indazol-5-yl) spiro[3H, indol-3, 2′ -thiazolidine]-2,4′-diones* ( 5a–i ).Item A facile synthesis of novel unsymmetrical bis-spiro[indole-pyrazolinyl-thiazolidine]-2,4'-diones (08-2933GP)(ARKAT, 2008-08-11) Sakhuja, RajeevAn elegant synthesis of some novel unsymmetrical bis-indol-2,3-diones (4a-d) has been achieved via 1-(6-bromohexyl)-1H-indol-2,3-diones (3a,b). These compounds have been further used for the synthesis of novel bis-spiroindoles (7a-d) via hitherto unknown bis Schiff‘s bases (6a-d).Item Synthesis of boltorn 1,2,3-triazole dendrimers by click chemistry(Wiley, 2009) Sakhuja, RajeevSecond-, third-, and fourth-generation hyperbranched aliphatic polyols namely Boltorn® H20, Boltorn H30, and Boltorn H40 were endcapped with azido and activated acetylenic groups in good to excellent yields (75–95%) following an acid catalyzed procedure. The resultant terminally functionalized dendritic azido and acetylenic groups undergo 1,3-dipolar cycloaddition using methyl (or ethyl) propiolate and benzyl azide, respectively, under catalytic or noncatalytic conditions below 40 °C to yield 1,2,3-triazole dendrimeric polymers in 82–95% yield, under extremely mild conditions that could be applied for compounds sensitive to acid, base, or heat. The dendritic azido and activated acetylenic derivatives may act as novel scaffolds to tune the mechanical properties of different polymers.Item Microwave Assisted Synthesis of Five Membered Azaheterocyclic Systems(Bentham Science, 2012) Sakhuja, Rajeev; Bajaj, KiranThe present review provides a comprehensive summary of microwave-assisted preparation of five-membered azaheterocyclic systems, such as pyrrole, pyrazole, imidazole, triazole, thiazole, isothiazole, oxazole, isoxazole, oxadiazole, thiadiazole and tetrazole.