Abstract
4-Methyl umbelliferone derivatives are synthesized and characterized by spectral and analytical techniques. A convenient one pot procedure has been reported for the preparation of 7-methoxy-4-methyl-8-(2-oxopropyl)-2H-chromene-2-one using reductive amination.
Similar content being viewed by others
References
Singh R, Singh B, Singh S, Kumar N, Kumar S (2010) Umbelliferone: an antioxidant isolated from Acacia nilotica (L.) Willd. Ex. Del. Food Chem 120:825–830
Vogel A (1820) Darstellung von Benzoesäure aus der Tonka-Bohne und aus den Meliloten-oder Steinklee-Blumen Gilbert’s. Ann Phys 64:161–166
Spath E (1937) The chemistry of coumarins. Chem Ber 70A:83–93
Suresh MS, Narsinh MS (1945) The chemistry of coumarins. Chem Revs 36:1–62
Bose PK (1958) Bio active natural products. J Indian Chem Soc 35:367–375
Dean FM (1963) Naturally occurring oxygen ring compounds. Butter Worth, London, pp 176–220
Soine TO (1964) The naturally occuring coumarins and related physiological activities. J Pharm Sci 53:231–264
Bourinbaiar AS, Nagorny R (1993) Human immunodeficiency virus type 1 infection of choriocarcinoma-derived trophoblasts. Acta Virol 37:21–28
Hoult JR, Forder RA, de las Heras B, Lobo IB, Paya M (1994) Inhibitory activity of a series of coumarins on leukocyte eicosanoid generation. Agents Actions 42:44–49
De Julian-Ortiz JV, Galvez J, Munoz-Collado C, Garcia-Domenech R, Gimeno-Cardona C (1999) Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds. J Med Chem 42:3308–3314
Farinola N, Piller N (2005) Pharmacogenomics: its role in re-establishing coumarin as treatment for lymphedema. Lymphat Res Biol 3:81–86
Zhang Lin, Li Meng-Yan, Wang Li-Wei, Gao Jie, Ma Chao-Mei (2013) Isolation, identification, quantification and inhibitory activity on HCV protease of coumarins from Viola yedoensis. Can Chem Trans 1(3):157–164
Lowenthal J, Birnbaum H (1969) Vitamin K and coumarin anticoagulants: dependence of anticoagulant effect on inhibition of vitamin K transport. Science 164:181–183
Mei HL, Yu SC, Yan JT, Duen SC (2011) Antioxidant properties of 5,7-dihydroxycoumarin derivatives in in vitro cell-free and cell-containing systems. J Exp Clin Med 3(3):126–131
Ufer M (2005) Comparative pharmakokinetics of Vit-K antagonist: warferin, phen-procoumarol acenocoumarol. Clin Pharmacokinet 44(12):1227–1246
Barcellona DI, Vannini ML, Fenu L, Balestrieri C, Marongiu F (1998) Warferin or acenocoumarol, which is better in management of oral anti coagulant. J Thromb Haemost 80(6):899–902
Maurer LH, Hendon JE, Hollis DR, Aisner J, Carey RW, Skarin AT (1997) Randamised trial of chemotheraupy and radiation therauphy with or with our warferin for limited stage small cell lung cancer. J Clin Oncol 15:3378–3387
Li T, Chang CY, Jin DY, Lin PJ, Khvorova A, Stafford DW (2004) Identification of gene for vitamin-K epoxide reductase. Nature 427(6974):541–544
Hoeksema H, Johnson JL, Hinman JW (1955) Structural studies on streptonivicin, a new antibiotic. J Am Chem Soc 77:6710–6711
Maxwell A, Lawson DM (2003) The ATP-binding site of type II topoisomerases as a target for antibacterial drugs. Curr Top Med Chem 3(3):283–303
Heide L (2009) Genetic engineering of antibiotic biosynthesis for the generation of new aminocoumarins. Biotechnol Adv 27(6):1006–1014
Samuels DS, Garon CF (1993) Coumermycin A1 inhibits growth and induces relaxation of supercoiled plasmids in Borrelia burgdorferi, the Lyme disease agent. Antimicrob Agents Chemother 37(1):46–50
Sylvie G, Pieter DC, Neil KL, Christopher WT (2005) Characterization of the formation of the pyrrole moiety during clorobiocin and coumermycin A1 biosynthesis. Biochemistry 44(8):2770–2780
Christine A, Shu-Ming L, Bernd K, Bertolt G, Lutz H (2007) New aminocoumarin antibiotics derived from 4-hydroxycinnamic acid are formed after heterologous expression of a modified clorobiocin biosynthetic gene cluster. J Antibiot 60:504–510
Jeong IG, You D, Yoon JH (2014) Impact of tamsulosin on urinary retention following early catheter removal after robot-assisted laparoscopic radical prostatectomy: a prospective randomized controlled trial. Int J Urol 21(2):164–168
Veld BA, van Puyenbroek E, Stricker BH (1997) Hypersensitivity reactions to use of mebeverine. Ned Tijdschr Geneeskd 141(28):1392–1395
Darzens G (1904) Method generale de synthese des aldehyde al’aide des acides glycidique substitues. C R 39:1214–1220
Anton V, Haack A (1927) U¨ ber die Einwirkung von Halogen-phosphor auf Alkyl-formanilide. Eine neue Methode zur 657 Darstellung sekunda¨rer und tertia¨rer p-Alkylamino-benzalde- 658 hyde. Ber Dtsch Chem Ges 60:119–127
Hurd CD, Webb CN (1941) Synthesis of p-dimethylamino benzophenone from the reaction of benzanilide and dimethylaniline. Org Synth Coll 1:217–218
Reimer K, Tiemann F (1876) Ueber die Einwirkung von Chloroform auf Phenole und besonders aromatische Oxysäuren in alkalischer Lösung. Ber Dtsch Chem Ges 9(2):1268–1278
Wynberg H (1991) The Reimer–Tiemann reaction. Compr Org Synth 2:769–775
Patel AD, Sharma MS, Vohra JJ, Joshi JD (1997) Synthesis, characterization and antimicrobial activities of binary and ternary complexes of UO2II and ThIV complexes with 5-hydroxymethyl-8-quinolinol and 8-formyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one with aniline. Indian Chem Soc 74:287–288
Michael B, Cadogan JIG, McNab Amish, Andrew MacPherson D, Peter Roddam V, Smith Carol, Helen Swenson R (1997) Synthesis of fused furans by gas-phase pyrolysis of 2-allyloxyarylpropenoic esters. J Chem Soc, Perkin Trans 1:2483–2493
Acknowledgments
The authors expressed his gratitude to Prof. A. G. Damu, Yogi Vemana University, Kadapa, India and Dr. S. Rajagopal, University of Hyderabad, Hyderabad, India for timely help and suggestions.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Karteek, S.D., Manidhar, D.M., Devarapally, A. et al. Synthesis of Some Novel 4-Methylumbelliferone Derivatives. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 86, 313–321 (2016). https://doi.org/10.1007/s40010-015-0263-8
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40010-015-0263-8