title: A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation.
abstract: A highly convenient method has been developed for the synthesis of (prop-2-ynyloxy) benzene and its derivatives. Differently substituted phenol and aniline derivatives were allowed to react with propargyl bromide in the presence of K2CO3 base and acetone as solvent. The compounds were synthesized in good yields (53-85%). Low cost, high yields and easy availability of compounds helped in the synthesis. Electron withdrawing groups favor the formation of stable phenoxide ion thus in turn favors the formation of product while electron donating groups do not favor the reaction. Phenol derivatives gave good yields as compared to that of aniline. As aprotic polar solvents favor SN2 type reactions so acetone provided best solvation for the reactions. K2CO3 was proved to be good for the synthesis. Antibacterial, Antiurease and NO scavenging activity of synthesized compounds were also examined. 4-bromo-2-chloro-1-(prop-2-ynyloxy)benzene 2a was found most active compound against urease enzyme with a percentage inhibition of 82.00±0.09 at 100 µg/mL with IC50 value of 60.2. 2-bromo-4-methyl-1-(prop-2-ynyloxy)benzene 2d was found potent antibacterial against Bacillus subtillus showing excellent inhibitory action with percentage inhibition of 55.67±0.26 at 100 µg/ml wih IC50 value of 79.9. Based on results, it can be concluded that some of the synthesized compounds may have potential antiurease and antibacterial effects against several harmful substances.
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad, Pakistan.
authors.forename: Tannaza
authors.initials: T
authors.lastname: Batool
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad, Pakistan.
authors.forename: Nasir
authors.initials: N
authors.lastname: Rasool
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad, Pakistan.
authors.forename: Yasmeen
authors.initials: Y
authors.lastname: Gull
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad, Pakistan.
authors.forename: Mnaza
authors.initials: M
authors.lastname: Noreen
authors.affiliation: Department of Chemistry, Islamia University of Bahawalpur, Bahawalpur, Pakistan.
authors.forename: Faiz-ul-Hassan
authors.initials: FU
authors.lastname: Nasim
authors.affiliation: Department of Chemistry, Islamia University of Bahawalpur, Bahawalpur, Pakistan.
authors.forename: Asma
authors.initials: A
authors.lastname: Yaqoob
authors.affiliation: Department of Chemistry, Government College University Faisalabad, Faisalabad, Pakistan.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Zubair
authors.affiliation: Deanship of scientific research, College of Engineering, King Saud University, Riyadh, Saudi Arabia.
authors.forename: Usman Ali
authors.initials: UA
authors.lastname: Rana
authors.affiliation: Deanship of scientific research, College of Engineering, King Saud University, Riyadh, Saudi Arabia.
authors.forename: Salah Ud-Din
authors.initials: SU
authors.lastname: Khan
authors.affiliation: The Patent Office, Karachi, Pakistan.
authors.forename: M
authors.initials: M
authors.lastname: Zia-Ul-Haq
authors.affiliation: Department of Crop Science, Faculty of Agriculture, 43400 UPM Serdang, Selangor, Malaysia.
authors.forename: Hawa Z E
authors.initials: HZ
authors.lastname: Jaafar
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000494:pharmacology; D010293:Pargyline / Q000031:analogs & derivatives / Q000737:chemistry; D010647:Phenyl Ethers / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000480:Alkynes; D000975:Antioxidants; D016166:Free Radical Scavengers; D010647:Phenyl Ethers; D010293:Pargyline; C458239:propargyl bromide