Aqueous-Mediated Ring Opening of Epoxides with Oximes: A Rapid Entry into β-Hydroxy Oxime <i>O</i>-Ethers as Potential β-Adrenergic Blocking Agents

Rad, Mohammad Navid Soltani; Behrouz, Somayeh; Dianat, Manije

doi:10.1055/s-2008-1067122

Cited by 13 publications

(7 citation statements)

References 8 publications

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“…Thus, epichlorohydrin and epibromohydrin under controlled conditions react with two different nucleophiles to afford a broad range of relevant organic compounds. Previously, we reported an efficient O-alkylation of oximes with epoxides using KOH in stirring H 2 O/DMSO (1:9, V/V) solution at room temperature [39]. Using this protocol, epichlorohydrin and/or epibromohydrin reacted with oximes 20a-20d to afford a mixture of the epoxides 21a-21d and halohydrins 22a-22d and/or 22 a-22 d. The O-oximation reaction with epichlorohydrin led to chlorohydrin as a major product, while epoxide was usually generated when the O-oximation reaction was achieved between oxime and epibromohydrin.…”

Section: Resultsmentioning

confidence: 99%

“…The oximation reaction was achieved using hydroxyl amine hydrochloride and NaOH in EtOH/H 2 O (9:1, V/V) at reflux conditions [33]. Oximes 20a-20d are capable to react with various sources of carbon electrophiles, especially with epoxides [39]. Among epoxides, the terminal epoxides comprising epichlorohydrin and epibromohydrin have received considerable attention in organic synthesis owing to their inherent properties as ambident electrophiles.…”

Section: Resultsmentioning

confidence: 99%

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Design, synthesis, and biological activities of novel azole-bonded $$\upbeta $$ β -hydroxypropyl oxime O-ethers

et al. 2014

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The synthesis and biological effects of 15 novel azole-bonded β-hydroxypropyl oxime O-ethers have been described. In this synthesis, the oximation of aromatic ketones followed by an O-alkylation reaction with epichlorohydrin and/or epibromohydrin led to the corresponding O-oxime ether adducts. Subsequently, the attained O-oxime ether adducts were used to synthesize the target molecules after treating them with the appropriate azole derivatives. The in vitro antifungal and antibacterial activities of title compounds were obtained against several pathogenic fungi, Gram-positive and/or Gram-negative bacteria. Benzophenone O-2-hydroxy-3-(2-phenyl-1 H-imidazol-1-yl) propyl oxime and 9H-fluoren-9-one O-2-hydroxy-3-(2-phenyl-1 H-imidazol-1-yl)propyl oxime proved to have considerable antifungal activity against Candida albicans, Candida krusei, Aspergillus niger, and Trichophyton rubrum. These two compounds demonstrated comparable antifungal activity to clotrimazole and fluconazole (standard drugs). All compounds were also tested against Escherichia coli and Staphylococcus aureus as Gram-negative and Gram-positive bacteria, respectively, and their activities were compared to gentamycin and ampicillin (reference drugs). In general, marginal antibacterial activity against tested bacteria was observed for the title compounds. A molecular docking study is also discussed for the two most potent compounds against fungi. The docking study reveals a considerable interaction between the two most potent compounds and the active site of Mycobacterium P450DM. Moreover, these two compounds are much strongly bound to the active site of Mycobacterium P450DM compared to fluconazole.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and biological activities of novel azole-bonded $$\upbeta $$ β -hydroxypropyl oxime O-ethers

et al. 2014

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“…to O-substituted oximes containing 1,2,3-triazole-1,4-diyl residues and in continuation of Soltani Rad and Behrouz et al research on design and synthesis of new b-adrenoceptor-antagonist analogs 23 as well as oxime chemistry, 29,30 Fig. 1.…”

Section: Introductionmentioning

confidence: 93%

‘Click Synthesis’ of Some Novel Benzimidazol Oxime Ethers Containing Heterocycle Residues as Potential ß‐Adrenergic Blocking Agents

Roeintan

Moosavi

Rad

et al. 2015

J Chinese Chemical Soc

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The 'click synthesis' of some novel O-substituted oximes, 5a-5j, which contain heterocycle residues, as new analogs of b-adrenoceptor antagonists is described (Scheme 1). The synthesis of these compounds was achieved in four steps. The formation of (E)-2-(1H-benzo[d]imidazol-1-yl)-1-phenylethanone oxime, followed by their reaction with 2-(chloromethyl)oxirane, afforded mixture of oil compounds 3 and 4, which by a subsequent tetra-n-butylammonium bromide (TBAB)-catalyzed reaction with N-H heterocycle compounds (Scheme 1), led to the target compounds 5a-5j in good yields.

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“…Oximes 4a -4i can react with diverse alkyl halides or other Celectrophiles. Oximes are known to be ambident nucleophiles [11] [12], i.e., the alkylation of oximes can take place at the O-atom to afford the O-alkyl derivatives or at the N-atom to generate nitrones [13]. Likewise, the site of alkylation of an oxime anion is affected by factors such as base and solvent type, the nature of the alkylating agent, the cation type, the geometry of the substrate, the functionality, the degree of dissociation of the oxime salt, etc.…”

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‘Click Synthesis’ of 1H‐1,2,3‐Triazolyl‐Based Oxiconazole (=(1Z)‐1‐(2,4‐Dichlorophenyl)‐2‐(1H‐imidazol‐1‐yl)ethanone O‐[(2,4‐Dichlorophenyl)methyl]oxime) Analogs

Rad

Asrari

Behrouz

et al. 2011

Helvetica Chimica Acta

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The click synthesis of some oxiconazole analogs 5a -5v having 1H-1,2,3-triazolyl residues by Huisgen cycloaddition was achieved in four steps (Scheme 1). Oximation of phenacyl chloride (1) followed by azidation of 2-chloro-1-phenylethanone oxime (2) provided azido ketoxime 3. The CuIcatalyzed Huisgen cycloaddition of 3 with terminal alkynes gave the 4-substituted (at the triazole) 2-(1H-1,2,3-triazol-1-yl)-1-phenylethanone oximes 4a -4i. The O-alkylation of 4a -4i with various alkyl halides resulted in the formation of the target molecules 5a -5v in good yields.Helvetica Chimica Acta -Vol. 94 (2011) Scheme 1. Synthesis of the 1H-1,2,3-Triazolyl-Based Oxiconazole Analogues 5a -5v Scheme 2. Terminal Alkynes from Propargyl Bromide and Nucleophiles

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Aqueous-Mediated Ring Opening of Epoxides with Oximes: A Rapid Entry into β-Hydroxy Oxime O-Ethers as Potential β-Adrenergic Blocking Agents

Cited by 13 publications

References 8 publications

Design, synthesis, and biological activities of novel azole-bonded $$\upbeta $$ β -hydroxypropyl oxime O-ethers

Design, synthesis, and biological activities of novel azole-bonded $$\upbeta $$ β -hydroxypropyl oxime O-ethers

‘Click Synthesis’ of Some Novel Benzimidazol Oxime Ethers Containing Heterocycle Residues as Potential ß‐Adrenergic Blocking Agents

‘Click Synthesis’ of 1H‐1,2,3‐Triazolyl‐Based Oxiconazole (=(1Z)‐1‐(2,4‐Dichlorophenyl)‐2‐(1H‐imidazol‐1‐yl)ethanone O‐[(2,4‐Dichlorophenyl)methyl]oxime) Analogs

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