A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation

PLoS ONE

Volumn 9, Issue 12, 2014, Pages

  Batool, Tannaza ^a   Rasool, Nasir ^a   Gull, Yasmeen ^a   Noreen, Mnaza ^a   Nasim, Faiz Ul Hassan ^b   Yaqoob, Asma ^b   Zubair, Muhammad ^a   Rana, Usman Ali ^c   Ud Din Khan, Salah ^c   Zia Ul Haq, M ^d   Jaafar, Hawa Z E ^e  

^a GOVERNMENT COLLEGE UNIVERSITY   (Pakistan)

^b THE ISLAMIA UNIVERSITY OF BAHAWALPUR   (Pakistan)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

^d The Patent Office   (Pakistan)

^e UNIVERSITY PUTRA MALAYSIA   (Malaysia)

Author keywords

[No Author keywords available]

Indexed keywords

(PROP 2 YNYLOXY)BENZENE DERIVATIVE; 2 BROMO 4 METHYL 1 (PROP 2 YNYLOXY)BENZENE; 4 BROMO 2 CHLORO 1 (PRO 2 YNYLOXY)BENZENE; ACETONE; ANILINE DERIVATIVE; BENZENE DERIVATIVE; BROMINE DERIVATIVE; PHENOL DERIVATIVE; POTASSIUM CARBONATE; PROPARGYL BROMIDE; UNCLASSIFIED DRUG; UREASE; ALKYNE; ANTIOXIDANT; DIPHENYL ETHER DERIVATIVE; PARGYLINE; SCAVENGER;

ANTIBACTERIAL ACTIVITY; ANTIUREASE ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; ENZYME INHIBITION; IC50; NONHUMAN; PROCESS OPTIMIZATION; SOLVATION; SUBSTITUTION REACTION; SYNTHESIS; ANALOGS AND DERIVATIVES; CHEMISTRY; DRUG EFFECTS; PROCEDURES;

ALKYNES; ANTIOXIDANTS; BACILLUS SUBTILIS; CHEMISTRY TECHNIQUES, SYNTHETIC; FREE RADICAL SCAVENGERS; PARGYLINE; PHENYL ETHERS;

EID: 84919941087     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0115457     Document Type: Article

References (39)

1. Meldal M, Tornoe CW (2008) Cu-Catalyzed Azide-Alkyne Cycloaddition. Chemical Reviews 108: 2952-3015.
2. Antoni P, Nystro D, Hawker CJ, Malkoch M (2007) A chemoselective approach for the accelerated synthesis of well-defined dendritic architectures. Chemical Communications 22: 2249-2251.
3. Wei L, Mulder JA, Xiong H, Zi CA, Douglas CJ, et al. (2001) Efficient preparations of novel ynamides and allenamides. Tetrahedron 57: 459-466.
4. Huang YJ, Ye YS, Yen YC, Tsai LD, Hwang BJ, et al. (2011) Synthesis and characterization of new sulfonated polytriazole proton exchange membrane by click reaction for direct methanol fuel cells (DMFCs). International Journal of Hydrogen Energy 36: 15333-15343.
5. He J, Feng L, Li J, Tao R, Wang F, et al. (2012) Design, synthesis and biological evaluation of novel 2-methylpyrimidine-4-ylamine derivatives as inhibitors of escherichia coli pyruvate dehydrogenase complex E1. Bioorganic & Medicinal Chemistry 20: 1665-1670.
6. Zhang Y, Wang G, Huang J (2011) Preparation of amphiphilic poly(ethylene oxide)-block-polystyrene macrocycles via glaser coupling reaction under cubr/pyridine system. Journal of Polymer Science Part A: Polymer Chemistry 49: 4766-4770.
7. Lee JW, Kim JH, Kim B-K, Kim JH, Shin WS, et al. (2006) Convergent synthesis of PAMAM-like dendrimers from azide-functionalized PAMAM dendrons. Bulletin of the Korean Chemical Society 27: 1795-1800.
8. Basak A, Pal R, Das S (2009) Synthesis of -lactam fused enediynes by intramolecular kinugasa reaction: comparison of reactivity with monocyclic analogues. International Journal of Chemistry 1: 63-74.
9. Krim J, Sillahi B, Taourirte M, Rakib EM, Engels JW (2009) Microwave-assisted click chemistry: synthesis of mono and bis-1,2,3-triazole acyclonucleoside analogues of acyclovir via copper (i)-catalyzed cycloaddition. Arkivoc 8: 142-152.
10. Joshi MC, Bisht GS, Rawat DS (2007) Syntheses and antibacterial activity of phendioxy substituted cyclic enediynes. Bioorganic & Medicinal Chemistry Letters 17: 3226-3230.
11. Kundu NG, Chaudhuri G, Upadhyay A (2001) Palladium-catalyzed heteroannulation leading to heterocyclic structures with two heteroatoms: a highly regio- and stereoselective synthesis of (Z)-4-alkyl-2-alkyl(aryl)idene-3,4-dihydro-2 H-1,4-benzoxazines and (Z)-3-alkyl(aryl)idene-4-tosyl-3,4-dihydro-2 H. The Journal of Organic Chemistry 66: 20-29.
12. Booth SE, Jenkins PR, Swain CJ, Sweeney JB (1994) Intramolecular addition of vinyl and aryl radicals to oxime ethers in the synthesis of five-, six- and seven-membered ring systems. Journal of the Chemical Society, Perkin Transactions 1 34: 99-102.
13. Samai S, Nadi GN, Singh MS (2010) An efficient and facile one pot synthesis of propargylamines by three-component coupling of aldehydes, amines and alkynes via C-H activation catalyzed by NiCl2.Tetrahedron Letters 51: 5555-5558.
14. Rostovstev VV, Green LG, Fokin VV, Sharpless KB (2002) A stepwise Huisgen cycloaddition process: Copper (I) catalyzed regioselective ligation of azides and terminal alkynes. Angewandte Chemie International Edition 41: 2596-2599.
15. Tornoe C, Christensen C, Medal M (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. Journal of Organic Chemistry 67: 3057-3064.
16. Agalave SG, Maujan SR, Pore VS (2011) Click chemistry: 1,2,3-Triazoles as pharmacophores. Chemistry-An Asian Journal 6: 2696-2718.
17. Speers AE, Adam GC, Cravatt BF (2003) Activity-based protein profiling in vivo using a copper (I)-catalyzed azide-alkyne [3+2] cycloaddition. Journal of American Chemical Society 125: 4686-4687.
18. Dabiri M, Salehi P, Bahramnejad M, Sherafat F (2010) Synthesis of diheterocyclic compounds based on triazolyl methoxy Phenylquinazolines via a one-pot four-component-click reaction. Journal of Combinatorial Chemistry 12: 638-642.
19. Quan ZJ, Quion X, Zhang Z, Da YX, Wang XC (2013) Copper-catalyzed click synthesis of functionalized 1,2,3-triazoles with 3,4-dihydropyrimidinone or amide group via a one-pot four-component reaction. Tetrahedron 69: 881-887.
20. Martin-Matute B, Nevado C, Cardenas DJ, Echavarren AM (2003) Intramolecular Reactions of Alkynes with Furans and Electron Rich Arenes Catalyzed by PtCl2: The Role of Platinum Carbenes as Intermediates. Journal of American Chemical Society 125: 5757-5766.
21. Agag T, Takeichi T (2001) Novel Benzoxazine Monomers Containing p-Phenyl Propargyl Ether: Polymerization of Monomers and Properties of Polybenzoxazines. Macromolecules 34: 7257-7263.
22. Pal M, Parasuraman K, Yeleswarapu KR (2003) Palladium-catalyzed cleavage of O/N-Propargyl protecting groups in aqueous media under a copper-free condition. Organic Letters 5: 349-352.
23. Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, et al. (2003) Biconjugation by Copper(I)-catalyzed azide-alkyne [3+2] cycloaddition. Journal of American Chemical Society 125: 3192-3193.
24. Bahulayan D, Arun S (2012) An easy two step synthesis of macrocyclic peptidotriazoles via a fourcomponent reaction and catalyzed intramolecular alkyne-azide [3+2] click cycloaddition. Tetrahedron Letters 53: 2850-2855.
25. Quan ZJ, Quion X, Zhang Z, Da YX, Wang XC (2013) Copper-catalyzed click synthesis of functionalized 1,2,3-triazoles with 3,4-dihydropyrimidinone or amide group via a one-pot four-component reaction. Tetrahedron 69: 881-887.
26. Alonso F, Moglie Y, Radivoy G, Yus M (2012) Multicomponent click synthesis of potentially biologically active triazoles catalyzed by copper nanoparticles on activated carbon in water. Heterocycles 84: 1033-1044.
27. Shargi H, Beyzavi MS, Safavi A,Doroodman M, Mohammad M, et al. (2009) Immobilization of porphyniratocopper nanoparticles onto activated multi-walled carbon nanotubes and a study of its catalytic activity as an efficient heterogeneous catalyst for a click approach to the three-component synthesis of triazoles in water. Advnced Synthesis Catalysis 351: 2391-2410.
28. Lee LV, Mitchell ML, Huang SJ, Fokin VV, Sharpless KB (2003) A potent and highly selective inhibitor of human a-1,3-Fucosyltransferase via click chemistry. Journal of American Chemical Society 125: 9588-9589.
29. Gull Y, Rasool N, Noreen M, Nasim F-U-H, Yaqoob A, et al. (2013) Efficient synthesis of 2-amino-6-arylbenzothiazoles via Pd(0) Suzuki cross coupling reactions: potent urease enzyme inhibition and nitric oxide scavenging activities of the products. Molecules 18: 8845-8857.
30. Serwar M, Akhtar T, Hameed S, Khan KM (2009) Synthesis, urease inhibition and antimicrobial activities of some chiral-5-aryl-4-(1-phenylpropyl)-2H-1,2,4-triazole-3(4H)-thiones. Arkivoc: 210-221.
31. Singh D, Mishra M, Gupta M, Singh P, Gupta A, et al. (2012) Original article nitric oxide radical scavenging assay of bioactive compounds present in methanol extract of Centella asiatica. International Journal of Pharmacy and Pharmaceutical Science Research 2: 42-44.
32. Chippada SC, Vangalapati M (2011) Antioxidant, anti-inflammatory and anti arthritic activity of Centella asiatica extracts. Journal of Chemical, Biological and Physical Sciences 1: 260-269.
33. Binder WH, Kluger C (2006) Azide/Alkyne-click reactions: Applications in material science and organic synthesis. Current Organic Chemistry 10: 1791-1815.
34. Yadav JS, Reddy SBV, Reddy GM, Anjum RS (2009) Cu(OTf)2/Cu-catalyzed four-component reaction: A facile synthesis of a-alkoxytriazoles via click chemistry. Tetrahedron Letters 50: 6029-6031.
35. Wu P, Feldman AK, Nugent AK, Hawker CJ, Scheel A, et al. (2004) Efficiency and fidelity in a click chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes. Angewandte Chemie International Edition 43: 3928-3932.
36. Mendoza-Espinosa D, Negron-Silva GE, Lomas-Romero L, Gutierrez-Carrillo A, Antillán R (2014) Pseudo-Four Component Synthesis of Mono- and Di-Benzylated-1,2,3-Triazoles Derived from Aniline. Molecules 19: 55-66.
37. Sokmen BB, Onar HC, Yusufoglu A (2012) Anti-elastase, anti-urease and antioxidant activities of (3-13)-monohydroxyeicosanoic acid isomers. Journal of the Serbian Chemical Society 77: 1353-1361.
38. Garrat DC (1964) The Quantitative analysis of Drugs. 3rd ed. Chapman & tall Japan.
39. Atta-ur-Rahman, Choudhary MI, Thomson WJ (2005) Bioassay techniques for drugs. Harward Academic Press. Amsterdam.