Lipase-catalyzed enantioseparation of alcohols containing a tetrazole ring

Łukowska-Chojnacka, Edyta; Bernaś, Urszula; Plenkiewicz, Jan

doi:10.1016/j.tetasy.2012.01.015

Cited by 7 publications

(5 citation statements)

References 43 publications

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“…There is no doubt, that repeated purification contributed to lower yields of the reactions (Table 1 ). In this case only 2,5-disubstituted tetrazoles were obtained, what is consistent with our previous studies [ 27 ].…”

Section: Resultssupporting

confidence: 93%

Synthesis of polybrominated benzimidazole and benzotriazole derivatives containing a tetrazole ring and their cytotoxic activity

et al. 2016

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A series of new benzimidazole and benzotriazole derivatives containing a tetrazole moiety was synthesized by N-alkylation of 5-aryltetrazole with 4,5,6,7-tetrabromo-1-(3-chloropropyl)-1H-benzimidazole and 4,5,6,7-tetrabromo-2-(3-chloropropyl)-2H-benzotriazole. The reaction was regioselective and mostly 2,5-disubstituted tetrazole derivatives were obtained. The effect of all synthesized compounds on human recombinant casein kinase 2alpha subunit (rhCK2α) and cytotoxicity against human T-cell lymphoblast (CCRF-CEM) and breast adenocarcinoma (MCF-7) cell lines were evaluated. The results have shown that many of the synthesized compounds exhibit significant cytotoxicity at micromolar concentration.Graphical abstract

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Section: Resultssupporting

confidence: 93%

Synthesis of polybrominated benzimidazole and benzotriazole derivatives containing a tetrazole ring and their cytotoxic activity

et al. 2016

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“…To date, a plethora of synthetically useful hydroxylated/acylated derivatives have been investigated as the racemic substrates for the lipase-catalyzed kinetic resolution (KR) and/or dynamic kinetic resolution (DKR). Among the most important are the secondary alcohols and the corresponding esters possessing (hetero)aromatic substituents, such as imidazole [31], 1,2,4-triazole [32][33][34], pyrazole [35], isoxazole [36], thiazole [37,38], tetrazole [39,40], thiophene [41,42], tetrahydrothiophene [43], furan [44][45][46][47], benzimidazole [48], benzotriazole [49,50], benzothiazole [51], benzothiophene [52,53], benzofuran [54][55][56], tetrahydrofuran [57], pyridine [58,59], piperidine [44,60], piperazine [61], pyrrolidine [62,63], pyran [64], quinoline [65], phenothiazine [66][67][68][69][70], 1,10-phenanthroline [71], 1,3-dimethylxanthine [72,73], azetidine…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of Optically Active Alcohols Possessing 1,2,3,4-Tetrahydroquinoline Moiety Employing Lipases or Variants of the Acyltransferase from Mycobacterium smegmatis

Zdun

Kopińska²,

Dranka³

et al. 2022

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The enzymatic kinetic resolution (EKR) of racemic alcohols or esters is a broadly recognized methodology for the preparation of these compounds in optically active form. Although EKR approaches have been developed for the enantioselective transesterification of a vast number of secondary alcohols or hydrolysis of their respective esters, to date, there is no report of bio- or chemo-catalytic asymmetric synthesis of non-racemic alcohols possessing 1,2,3,4-tetrahydroquinoline moiety, which are valuable building blocks for the pharmaceutical industry. In this work, the kinetic resolution of a set of racemic 1,2,3,4-tetrahydroquinoline-propan-2-ols was successfully carried out in neat organic solvents (in the case of CAL-B and BCL) or in water (in the case of MsAcT single variants) using immobilized lipases from Candida antarctica type B (CAL-B) and Burkholderia cepacia (BCL) or engineered acyltransferase variants from Mycobacterium smegmatis (MsAcT) as the biocatalysts and vinyl acetate as irreversible acyl donor, yielding enantiomerically enriched (S)-alcohols and the corresponding (R)-acetates with E-values up to 328 and excellent optical purities (>99% ee). In general, higher ee-values were observed in the reactions catalyzed by lipases; however, the rates of the reactions were significantly better in the case of MsAcT-catalyzed enantioselective transesterifications. Interestingly, we have experimentally proved that enantiomerically enriched 1-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)propan-2-ol undergoes spontaneous amplification of optical purity under achiral chromatographic conditions.

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“…14 The number of synthetic benzoxazole derivatives is enormous, and they exhibit various types of activity eg, antibacterial, antifungal, antiinflammatory, antiviral, anticancer, analgesic, anticonvulsant, antioxidant, antidepressant, anthelmintic, and herbicidal. [49][50][51] Taking into consideration a wide pharmacological potential of compounds containing benzoxazole moiety and our interest in the enzyme-catalyzed kinetic resolution (KR) of azole derivatives, [52][53][54] we present studies on the chemoenzymatic synthesis of new benzoxazole derivatives. 40 There are also benzoxazole derivatives, which are potent 5-HT 3 receptor antagonists.…”

Section: Introductionmentioning

confidence: 99%

“…[46][47][48] Other benzoxazole derivatives exhibiting a promising tuberculostatic activity are also described. [49][50][51] Taking into consideration a wide pharmacological potential of compounds containing benzoxazole moiety and our interest in the enzyme-catalyzed kinetic resolution (KR) of azole derivatives, [52][53][54] we present studies on the chemoenzymatic synthesis of new benzoxazole derivatives. Two enzymatic approaches were applied to obtain the optically active molecules with benzoxazole nucleus: a lipase-catalyzed transesterification of appropriate alcohols and a lipase-catalyzed hydrolysis of corresponding esters.…”

Section: Introductionmentioning

confidence: 99%

Lipase‐catalyzed kinetic resolution of novel antitubercular benzoxazole derivatives

2017

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Novel benzoxazole derivatives were synthesized, and their antitubercular activity against sensitive and drug-resistant Mycobacterium tuberculosis strains (M. tuberculosis H Rv, M. tuberculosis sp. 210, M. tuberculosis sp. 192, Mycobacterium scrofulaceum, Mycobacterium intracellulare, Mycobacterium fortuitum, Mycobacterium avium, and Mycobacterium kansasii) was evaluated. The chemical step included preparation of ketones, alcohols, and esters bearing benzoxazole moiety. All racemic mixtures of alcohols and esters were separated in Novozyme SP 435-catalyzed transesterification and hydrolysis, respectively. The transesterification reactions were carried out in various organic solvents (tert-butyl methyl ether, toluene, diethyl ether, and diisopropyl ether), and depending on the solvent, the enantioselectivity of the reactions ranged from 4 to >100. The enzymatic hydrolysis of esters was performed in 2 phase tert-butyl methyl ether/phosphate buffer (pH = 7.2) system and provided also enantiomerically enriched products (ee 88-99%). The antitubercular activity assay has shown that synthesized compounds exhibit an interesting antitubercular activity. Racemic mixtures of alcohols, (±)-4-(1,3-benzoxazol-2-ylsulfanyl)butan-2-ol ((±)-3a), (±)-4-[(5-bromo-1,3-benzoxazol-2-yl)sulfanyl]butan-2-ol ((±)-3b), and (±)-4-[(5,7-dibromo-1,3-benzoxazol-2-yl)sulfanyl]butan-2-ol ((±)-3c), displayed as high activity against M. scrofulaceum, M. intracellulare, M. fortuitum, and M. kansasii as commercially available antituberculosis drug-Isoniazid. Moreover, these compounds exhibited twice higher activity toward M. avium (MIC 12.5) compared with Isoniazid (MIC 50).

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Lipase-catalyzed enantioseparation of alcohols containing a tetrazole ring

Cited by 7 publications

References 43 publications

Synthesis of polybrominated benzimidazole and benzotriazole derivatives containing a tetrazole ring and their cytotoxic activity

Synthesis of polybrominated benzimidazole and benzotriazole derivatives containing a tetrazole ring and their cytotoxic activity

Chemoenzymatic Synthesis of Optically Active Alcohols Possessing 1,2,3,4-Tetrahydroquinoline Moiety Employing Lipases or Variants of the Acyltransferase from Mycobacterium smegmatis

Lipase‐catalyzed kinetic resolution of novel antitubercular benzoxazole derivatives

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