Morita-Baylis-Hillman Reaction of 3-formyl-9-pyrido[3,4-]indoles and Fluorescence Studies of the Products

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2022 Aug 12

PMID 35957752

Authors

Nisha Devi

Virender Singh

Affiliations

Soon will be listed here.

Abstract

β-Carboline is a privileged class of the alkaloid family and is associated with a broad spectrum of biological properties. 3-Formyl-9-pyrido[3,4-]indole is a such potent precursor belonging to this family which can be tailored for installing diversity at various positions of β-carboline to generate unique molecular hybrids of biological importance. The present work is a step towards this and assimilates the results related to the exploration of 3-formyl-9-β-carbolines for the synthesis of β-carboline C-3 substituted MBH adducts followed by evaluation of their fluorescent characteristic. The effect of contact time, solvent system, concentration and substituents was also studied during investigation of fluorescence properties of these derivatives.

References

Ishikura M, Abe T, Choshi T, Hibino S . Simple indole alkaloids and those with a non-rearranged monoterpenoid unit. Nat Prod Rep. 2013; 30(5):694-752. DOI: 10.1039/c3np20118j. View

Abdelmohsen U, Bayer K, Hentschel U . Diversity, abundance and natural products of marine sponge-associated actinomycetes. Nat Prod Rep. 2014; 31(3):381-99. DOI: 10.1039/c3np70111e. View

Kamal A, Srinivasulu V, Nayak V, Sathish M, Shankaraiah N, Bagul C . Design and synthesis of C3-pyrazole/chalcone-linked beta-carboline hybrids: antitopoisomerase I, DNA-interactive, and apoptosis-inducing anticancer agents. ChemMedChem. 2014; 9(9):2084-98. DOI: 10.1002/cmdc.201300406. View

Higuchi K, Kawasaki T . Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat Prod Rep. 2007; 24(4):843-68. DOI: 10.1039/b516351j. View

Maksay G, Simonyi M . Benzodiazepine anticonvulsants accelerate and beta-carboline convulsants decelerate the kinetics of [35S]TBPS binding at the chloride ionophore. Eur J Pharmacol. 1985; 117(2):275-8. DOI: 10.1016/0014-2999(85)90614-4. View

Basavaiah D, Rao A, Satyanarayana T . Recent advances in the Baylis-Hillman reaction and applications. Chem Rev. 2003; 103(3):811-92. DOI: 10.1021/cr010043d. View

Wang Y, Tang J, Wang R, Yang L, Dong Z, Du L . Flazinamide, a novel beta-carboline compound with anti-HIV actions. Biochem Biophys Res Commun. 2007; 355(4):1091-5. DOI: 10.1016/j.bbrc.2007.02.081. View

Zhu Y, Liu M, Cai Q, Jia F, Wu A . A cascade coupling strategy for one-pot total synthesis of β-carboline and isoquinoline-containing natural products and derivatives. Chemistry. 2013; 19(31):10132-7. DOI: 10.1002/chem.201301734. View

Royer J, Bonin M, Micouin L . Chiral heterocycles by iminium ion cyclization. Chem Rev. 2004; 104(5):2311-52. DOI: 10.1021/cr020083x. View

10.

Guan H, Chen H, Peng W, Ma Y, Cao R, Liu X . Design of beta-carboline derivatives as DNA-targeting antitumor agents. Eur J Med Chem. 2006; 41(10):1167-79. DOI: 10.1016/j.ejmech.2006.05.004. View

11.

England D, Padwa A . Gold-catalyzed cycloisomerization of N-Propargylindole-2-carboxamides: application toward the synthesis of lavendamycin analogues. Org Lett. 2008; 10(16):3631-4. DOI: 10.1021/ol801385h. View

12.

Ishikura M, Abe T, Choshi T, Hibino S . Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat Prod Rep. 2015; 32(10):1389-471. DOI: 10.1039/c5np00032g. View

13.

Rook Y, Schmidtke K, Gaube F, Schepmann D, Wunsch B, Heilmann J . Bivalent beta-carbolines as potential multitarget anti-Alzheimer agents. J Med Chem. 2010; 53(9):3611-7. DOI: 10.1021/jm1000024. View

14.

Kamal A, Narasimha Rao M, Swapna P, Srinivasulu V, Bagul C, Shaik A . Synthesis of β-carboline-benzimidazole conjugates using lanthanum nitrate as a catalyst and their biological evaluation. Org Biomol Chem. 2014; 12(15):2370-87. DOI: 10.1039/c3ob42236d. View

15.

Chandrasekhar D, Borra S, Nanubolu J, Maurya R . Visible Light Driven Photocascade Catalysis: Ru(bpy)3(PF6)2/TBHP-Mediated Synthesis of Fused β-Carbolines in Batch and Flow Microreactors. Org Lett. 2016; 18(12):2974-7. DOI: 10.1021/acs.orglett.6b01321. View

16.

Maw G, Allerton C, Gbekor E, Million W . Design, synthesis and biological activity of beta-carboline-based type-5 phosphodiesterase inhibitors. Bioorg Med Chem Lett. 2003; 13(8):1425-8. DOI: 10.1016/s0960-894x(03)00159-8. View

17.

Zhang M, Sun D . Recent Advances of Natural and Synthetic β-Carbolines as Anticancer Agents. Anticancer Agents Med Chem. 2014; 15(5):537-47. DOI: 10.2174/1871520614666141128121812. View

18.

Langer P, Anders J, Weisz K, Jahnchen J . Efficient synthesis of 2-alkylidene-3-iminoindoles, indolo[1,2-b]isoquinolin-5-ones, delta-carbolines, and indirubines by domino and sequential reactions of functionalized nitriles. Chemistry. 2003; 9(16):3951-64. DOI: 10.1002/chem.200204566. View

19.

Pumphrey A, Dong H, Driver T . Rh(II)2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides. Angew Chem Int Ed Engl. 2012; 51(24):5920-3. PMC: 3397914. DOI: 10.1002/anie.201201788. View

20.

Basavaiah D, Reddy B, Badsara S . Recent contributions from the Baylis-Hillman reaction to organic chemistry. Chem Rev. 2010; 110(9):5447-674. DOI: 10.1021/cr900291g. View