Microwave-assisted synthesis, molecular docking and antimicrobial activity of novel 2-(3-aryl,1-phenyl-1H-pyrazol-4-yl)-8H-pyrano[2,3-f]chromen-4-ones

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• 作者：Dongamanti Ashok ; Kavitha Rangu ; Velagapuri Hanumantha Rao…
• 关键词：Pyran ; Pyrazole ; Chromenone ; Microwave irradiation ; Molecular docking ; Antimicrobial activity
• 刊名：Medicinal Chemistry Research
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：25
• 期：3
• 页码：501-514
• 全文大小：1,654 KB
• 参考文献：Ajay K, Poonam L, Deepak KA, Girish KG, Dhirender K, Om P (2012) Design, synthesis, computational and biological evaluation of some new hydrazino derivatives of DHA and pyranopyrazoles. Eur J Med Chem 50:81–89CrossRef
  Akbas E, Berber I (2005) Antibacterial and antifungal activities of new pyrazolo[3,4-d]pyridazin derivatives. Eur J Med Chem 40:401–405CrossRef PubMed
  Ammar NM, El-Diwany AI (1988) Antimicrobial study of Tephrosia nubica flavones. J Islamic Acad Sci 1:72–73
  Ashok D, Mohan Gandhi D, Srinivas G, Vikas Kumar A (2014) Microwave-assisted synthesis of novel 1,2,3-triazole derivatives and their antimicrobial activity. Med Chem Res 23:3005–3018CrossRef
  Bae EA, Han MJ, Lee M, Kim DH (2000) In vitro inhibitory effect of some flavonoids on rotavirus infectivity. Biol Pharm Bull 23:1122–1124CrossRef PubMed
  Benson HJ (1990) Microbiological applications, 5th edn. W. C. Brown Publications, Boston
  Birt DF, Hendrich S, Wang W (2001) Dietary agents in cancer prevention: flavonoids and isoflavonoids. Pharmacol Ther 90:157–177CrossRef PubMed
  Burka JM, Bower KS, Vanroekel RC, Stutzman RD, Kuzmowych CP, Howard RS (2005) The effect of fourth-generation fluoroquinolones gatifloxacin and moxifloxacin on epithelial healing following photorefractive keratectomy. Am J Ophthalmol 140:83–87CrossRef PubMed
  Chan-Bacab MJ, Petia-Rodriguez LM (2001) Plant natural products with leishmanicidal activity. Nat Prod Rep 18:674–688CrossRef PubMed
  Chou LC, Huang LJ, Yang JS, Lee FY, Teng CM, Kuo SC (2007) Synthesis of furopyrazole analogs of 1-benzyl-3-(5-hydroxymethyl-2-furyl)indazole (YC-1) as novel anti-leukemia agents. Bioorg Med Chem 15:1732–1740CrossRef PubMed
  Daidone G, Raffa D, Maggio B, Raimondi MV, Plescia F, Schillaci D (2004) Synthesis and antiproliferative activity of triazenoindazoles and triazenopyrazoles: a comparative study. Eur J Med Chem 39:219–224CrossRef PubMed
  Edwards MJ, Flatman RH, Mitchenall LA, Stevenson CEM, Le TBK, Clarke TA, Mckay AR, Fiedler HP, Buttner MJ, Lawson DM, Maxwell A (2009) A crystal structure of the bifunctional antibiotic simocyclinone D8, bound to DNA gyrase. Science 326:1415–1418CrossRef PubMed
  El-Saghier AMM, Naili MB, Rammash BK, Saleh NA, Kreddan KM (2007) Synthesis and anti bacterial activity of some new fused chromenes. ARKIVOC 16:83–91
  Friesner RA et al (2004) Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 47:1739–1749CrossRef PubMed
  Gerwick WH (1989) 6-Desmethoxyhormothamnione, a new cytotoxic styrylchromone from the marine cryptophyte Chrysophaeum taylori. J Nat Prod 52:252–256CrossRef PubMed
  Grassmann J, Hippeli S, Elstner EF (2002) Plant’s defence and its benefits for animals and medicine: role of phenolics and terpenoids in avoiding oxygen stress. Plant Physiol Biochem 40:471–478CrossRef
  Halliwell B, Aeshbach R, Loliger J, Aruoma OI (1995) The characterization of antioxidants. Food Chem Toxicol 33:601–617CrossRef PubMed
  Hamilton Miller JMT (1995) Antimicrobial properties of tea (Camellia sinensis L.). Antimicrob Agents Chemother 39:2375–2377PubMedCentral CrossRef PubMed
  Han C (1997) Screening of anticarcinogenic ingredients in tea polyphenols. Cancer Lett 114:153–158CrossRef PubMed
  Harborne JB (1999) Recent advances in chemical ecology. Nat Prod Rep 16:509–523CrossRef PubMed
  Holla BS, Mahalinga M, Karthikeyan MS, Akberali PM, Shetty NS (2006) Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents. Bioorg Med Chem 14:2040–2047CrossRef PubMed
  Isogi Gamill RB, Day CE, Schurr PE (1983) Khellin analogues. 1. General topological requirements for lipid-altering activity in furochromones. J Med Chem 26:1672–1674CrossRef
  Jain A, Martin MC, Parveen N, Khan NU, Parish JH, Hadi SM (1999) Reactivities of flavonoids with different hydroxyl substituents for the cleavage of DNA in the presence of Cu(II). Phytother Res 13:609–612CrossRef PubMed
  Li J, Zhao YF, Zhao XL, Yuan XY, Gong P (2006) Synthesis and anti-tumor activities of novel pyrazolo[1,5-a]pyrimidines. Arch Pharm Chem Life Sci 339:593–597CrossRef
  Marrison LR, Dickinson JM, Fairlamb IJS (2003) Suzuki cross-coupling approaches to the synthesis of bioactive 3-substituted and 5-substituted-4-methoxy-6-methyl-2-pyrones. Bioorg Med Chem Lett 13:2667–2671CrossRef PubMed
  Matsuo N, Yamada K, Yamashita K, Shoji K, Mori M, Sugano M (1996) Inhibitory effect of tea polyphenols on histamine and leukotriene B4 release from rat peritoneal exudate cells. In Vitro Cell Dev Biol Anim 32:340–344CrossRef PubMed
  Mehdi K, Farzaneh G, Hamid N, Alireza M, Morteza PH, Farshad HM, Saeed E, Mohsen V, Reza Z, Alireza F, Abbas S (2015) New tetracyclic tacrine analogs containing pyrano[2,3-c]pyrazole: efficient synthesis, biological assessment and docking simulation study. Eur J Med Chem 89:296–303CrossRef
  Miura S, Watanble J, Sano M, Tomita T, Osawa T, Hara Y, Tomita I (1995) Effects of various natural antioxidants on the Cu (2+)-mediated oxidative modification of low density lipoprotein. Biol Pharm Bull 18:1–4CrossRef PubMed
  Narender T, Tanvir SK, Rao MS, Srivastava K, Puri SK (2005) Prenylated chalcones isolated from Crotalaria genus inhibits in vitro growth of the human malaria parasite Plasmodium falciparum. Bioorg Med Chem Lett 15:2453–2455CrossRef PubMed
  Pham TA, Che H, Phan PT, Lee JW, Kim SS, Park H (2012) Oroxylin A analogs exhibited strong inhibitory activities against iNOS-mediated nitric oxide (NO) production. Bioorg Med Chem Lett 22:2534–2535CrossRef PubMed
  Sánchez I, Gómez-Garibay F, Taboada J, Ruiz BH (2000) Antiviral effect of flavonoids on the dengue virus. Phytother Res 14:89–92CrossRef PubMed
  Schrödinger LLC (2005) Glide, Version 4.0. New York, NY
  Shaveta AmrinderS, Matinder K, Surbhi S, Rajbir B, Singh Palwinder (2014) Rational design, synthesis and evaluation of chromone–indole and chromone–pyrazole based conjugates: identification of a lead for antiinflammatory drug. Eur J Med Chem 77:185–192CrossRef PubMed
  Singh SB, Kaelin DE, Wu J, Miesel L, Tan CM, Meinke PT, Olsen D, Lagrutta A, Bradley P, Lu J, Patel S, Rickert KW, Smith RF, Soisson S, Wei C, Fukuda H, Kishii R, Takei M, Fukuda Y (2014) Oxabicyclooctane-linked novel bacterial topoisomerase inhibitors as broad spectrum antibacterial agents. ACS Med Chem Lett 5:609–614PubMedCentral CrossRef PubMed
  Song SQ, Zhou LG, Li D, Tang D, Li JQ, Jiang WB (2004) Antifungal activity of five plants. Xinjiang Nat Prod Res Dev 16:157–159
  Sreenivas P (2011) Synthesis and antibacterial activity of some new spiro[pyrano[2,3-f]chromene-2,1′-cycloalkan]-4-ones and 1′-alkylspiro[pyrano[2,3-f]chromene-2,4′-piperidin]-4-ones. Indian J Chem Sect B 50B(10):1484–1490
  Wu H, Wang XH, Yic Leeb YHKH (2003) Anti-AIDS agents 54. A potent anti-HIV chalcone and flavonoids from genus Desmos. Bioorg Med Chem Lett 13:1813–1815CrossRef PubMed
  Xu HX, Lee SF (2001) Activity of plant flavonoids against antibiotic-resistant bacteria. Phytother Res 15:39–43CrossRef PubMed
  Yamada J, Tomita Y (1994) Enhancing effect of ascorbic acid on the mutagenicity of Trp-P-1 by indigocarmine in the Salmonella microsome. Biosci Biotechnol Biochem 58:2197–2200CrossRef
  Yamashita A (1985) Total synthesis of khellin via a chromium carbene complex. J Am Chem Soc 107:5823–5824CrossRef
  Yan RZ, Liu XY, Xu WF, Pannecouque C, Witvrouw M, De Clercq E (2006) Synthesis and anti-HIV evaluation of the novel 2-(m-chlorobenzyl)-4-substituted-7-methyl-1,1,3-trioxo-pyrazolo[4,5-e][1,2,4]thiadiazines. Arch Pharm Res 29:957–962CrossRef PubMed
  
• 作者单位：Dongamanti Ashok (1)
  Kavitha Rangu (1)
  Velagapuri Hanumantha Rao (1)
  Srinivas Gundu (1)
  Ballu Srilata (2)
  Manga Vijjulatha (2)
  
  1. Green and Medicinal Chemistry Lab, Department of Chemistry, Osmania University, Hyderabad, 500 007, India
  2. Molecular Modeling and Medicinal Chemistry Group, Department of Chemistry, Osmania University, Hyderabad, 500 007, India
  
• 刊物主题：Pharmacology/Toxicology; Biochemistry, general; Cell Biology;
• 出版者：Springer US
• ISSN：1554-8120

文摘

An efficient synthetic protocol of microwave-assisted synthesis of some novel 2-(3-aryl,1-phenyl-1H-pyrazol-4-yl)-8H-pyrano[2,3-f]chromen-4-ones 6a–j in excellent yields starting from 3-(3-aryl,1-phenyl-1H-pyrazol-4-yl)-1-(5-hydroxy-2H-chromen-6-yl)-propenones 5a–j was described. This approach offers the advantages of short reaction time (3–5 min), mild reaction conditions, high yields (80–88 %) and convenient operation. All the synthesized compounds were tested in vitro for their antimicrobial activity. The compounds 5h (Ar = 3-ethoxyphenyl), 6c (Ar = 4-chlorophenyl), 6e (Ar = 4-hydroxyphenyl) and 6i (Ar = 3,4-methoxyphenyl) were found to be potent against tested bacterial strains, and compounds 5g (Ar = 4-ethoxyphenyl), 6c (Ar = 4-chlorophenyl) and 6i (Ar = 3,4-methoxyphenyl) were found to be potent against tested fungal strains. The final compounds were subjected to molecular docking studies for the inhibition of enzyme DNA gyrase. The in silico molecular docking results are matching with the in vitro antimicrobial studies, and they may be considered as good inhibitor of DNA gyrase. Keywords Pyran Pyrazole Chromenone Microwave irradiation Molecular docking Antimicrobial activity