ACI/EG Eutectic Mixture Mediated Synthesis, Characterization and Osteoblast Differentiation Assessment of Spiropyrrolo[1,2-]isoquinoline Analogues

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 11

PMID 35542235

Authors

Govindasami Periyasami

Natarajan Arumugam

Mostafizur Rahaman

Raju Suresh Kumar

Muthurangan Manikandan

Musaad A Alfayez

Dhanaraj Premnath

Ali Aldalbahi

Affiliations

Soon will be listed here.

Abstract

An eco-friendly acetylcholine iodide-ethylene glycol (ACI/EG) deep eutectic mixture mediated green protocol has been developed for the synthesis of hitherto unexplored multi-functionalized linear tricyclic spiropyrrolo[1,2-]isoquinoline analogues. The effects of the synthesized compounds on the osteoblast differentiation of hBMSC-TERT cell lines were investigated and promising results were observed with significant IC values. In addition, molecular modeling simulations were also performed with the 3D structure of BMP-2 to reveal binding interactions and orientations of highly potent spiropyrrolo[1,2-]isoquinoline analogues.

Citing Articles

An expeditious and environmentally benign synthesis of dispiro-3-phenylpyrrolothiazoles in ACI/EG eutectic mixture and its antioxidant and antimicrobial activities against urinary tract pathogens.

Periyasami G, Ponmurugan K, Arumugam N, Sureshkumar R, Rahaman M, Periyan D BMC Chem. 2019; 13(1):42.

PMID: 31384790 PMC: 6661829. DOI: 10.1186/s13065-019-0553-3.

References

Ranjith Kumar R, Perumal S, Manju S, Bhatt P, Yogeeswari P, Sriram D . An atom economic synthesis and antitubercular evaluation of novel spiro-cyclohexanones. Bioorg Med Chem Lett. 2009; 19(13):3461-5. DOI: 10.1016/j.bmcl.2009.05.018. View

Domingo L, Picher M, Andres J, Oliva M . Theoretical Study on the Molecular Mechanism of the Domino Cycloadditions between Dimethyl Acetylenedicarboxylate and Naphthaleno- and Anthracenofuranophane. J Org Chem. 2001; 64(9):3026-3033. DOI: 10.1021/jo981442k. View

Zhu Y, Huang S, Tan B, Sun J, Whiteman M, Zhu Y . Antioxidants in Chinese herbal medicines: a biochemical perspective. Nat Prod Rep. 2004; 21(4):478-89. DOI: 10.1039/b304821g. View

Senwar K, Sharma P, Reddy T, Jeengar M, Nayak V, Naidu V . Spirooxindole-derived morpholine-fused-1,2,3-triazoles: Design, synthesis, cytotoxicity and apoptosis inducing studies. Eur J Med Chem. 2015; 102:413-24. DOI: 10.1016/j.ejmech.2015.08.017. View

Zhao X, Maddali K, Marchand C, Pommier Y, Burke Jr T . Diketoacid-genre HIV-1 integrase inhibitors containing enantiomeric arylamide functionality. Bioorg Med Chem. 2009; 17(14):5318-24. PMC: 2747503. DOI: 10.1016/j.bmc.2009.05.008. View

Nielsen T, Meldal M . Solid-phase synthesis of pyrroloisoquinolines via the intramolecular N-acyliminium Pictet-Spengler reaction. J Comb Chem. 2005; 7(4):599-610. DOI: 10.1021/cc050008a. View

Simonsen J, Rosada C, Serakinci N, Justesen J, Stenderup K, Rattan S . Telomerase expression extends the proliferative life-span and maintains the osteogenic potential of human bone marrow stromal cells. Nat Biotechnol. 2002; 20(6):592-6. DOI: 10.1038/nbt0602-592. View

Lee J, Mase N, Yonezawa T, Seo H, Jeon W, Cha B . Palmatine attenuates osteoclast differentiation and function through inhibition of receptor activator of nuclear factor-κb ligand expression in osteoblast cells. Biol Pharm Bull. 2010; 33(10):1733-9. DOI: 10.1248/bpb.33.1733. View

Yamaguchi A, Komori T, Suda T . Regulation of osteoblast differentiation mediated by bone morphogenetic proteins, hedgehogs, and Cbfa1. Endocr Rev. 2000; 21(4):393-411. DOI: 10.1210/edrv.21.4.0403. View

10.

Vila C, Lau J, Rueping M . Visible-light photoredox catalyzed synthesis of pyrroloisoquinolines via organocatalytic oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade with Rose Bengal. Beilstein J Org Chem. 2014; 10:1233-8. PMC: 4077507. DOI: 10.3762/bjoc.10.122. View

11.

Sashidhara K, Modukuri R, Jadiya P, Dodda R, Kumar M, Sridhar B . Benzofuran-chalcone hybrids as potential multifunctional agents against Alzheimer's disease: synthesis and in vivo studies with transgenic Caenorhabditis elegans. ChemMedChem. 2014; 9(12):2671-84. DOI: 10.1002/cmdc.201402291. View

12.

Gothelf K, Anker Jorgensen K . Asymmetric 1,3-Dipolar Cycloaddition Reactions. Chem Rev. 2002; 98(2):863-910. DOI: 10.1021/cr970324e. View

13.

Sakai T, Eskander R, Guo Y, Kim K, Mefford J, Hopkins J . Flavokawain B, a kava chalcone, induces apoptosis in synovial sarcoma cell lines. J Orthop Res. 2012; 30(7):1045-50. PMC: 3685290. DOI: 10.1002/jor.22050. View

14.

Feng C, Su J, Yan Y, Guo F, Wang Z . Cobalt-catalyzed oxidative [3 + 2] cycloaddition reactions: an efficient synthesis of pyrrolo- and imidazo-[2,1-a]isoquinolines. Org Biomol Chem. 2013; 11(39):6691-4. DOI: 10.1039/c3ob41424h. View

15.

Scarfi S . Use of bone morphogenetic proteins in mesenchymal stem cell stimulation of cartilage and bone repair. World J Stem Cells. 2016; 8(1):1-12. PMC: 4723717. DOI: 10.4252/wjsc.v8.i1.1. View

16.

Alexander S, Benson H, Faccenda E, Pawson A, Sharman J, Spedding M . The Concise Guide to PHARMACOLOGY 2013/14: catalytic receptors. Br J Pharmacol. 2014; 170(8):1676-705. PMC: 3892291. DOI: 10.1111/bph.12449. View

17.

Zhang Q, De Oliveira Vigier K, Royer S, Jerome F . Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev. 2012; 41(21):7108-46. DOI: 10.1039/c2cs35178a. View

18.

Velazquez-Campoy A, Todd M, Freire E . HIV-1 protease inhibitors: enthalpic versus entropic optimization of the binding affinity. Biochemistry. 2000; 39(9):2201-7. DOI: 10.1021/bi992399d. View

19.

Ihmels H, Mattay J, May F, Thomas L . Photoswitchable DNA-binding properties of a photochromic spirooxazine derivative. Org Biomol Chem. 2013; 11(31):5184-8. DOI: 10.1039/c3ob40930a. View

20.

Zhou B, Xing C . Diverse Molecular Targets for Chalcones with Varied Bioactivities. Med Chem (Los Angeles). 2016; 5(8):388-404. PMC: 4718574. DOI: 10.4172/2161-0444.1000291. View