Synthetic Access to New Carbamate and Thiocarbamate Derivatives from Pyridinecarbaldehyde Oximes and Hydroxypyridines

Koçak, Ahmet; Ahmetli, Gülnare; Koçak, Nuriye; Malkondu, Sait; Yaylaci, Aysegul; Kurbanli, Sultan

doi:10.1080/00397911.2010.490627

Cited by 3 publications

(3 citation statements)

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“…Interestingly, although carbamates are important in both medicinal and polymer chemistry, besides compound 23 [61], all the rest were new. Compounds 8-13 were produced as a sole product, bearing the Z-conformation [9,43,62].…”

Section: Synthesismentioning

confidence: 99%

“…In the case of aldoxime carbamates three reactions gave mixtures of inseparable Z-stereoisomers ≈10% along with the major E-stereoisomer (products 25-27). It has been noted in the literature the preferable E-conformation for oxime carbamates [61,64,65] where 1 H NMR spectroscopy has been used in order to distinguish between the two [61,65]. Thus, the imine benzylic proton of the E-stereoisomers shows a singlet in the area 8-8.7 ppm, whereas the ones belonging to a Z-conformation are upfield and appear between 7.3-7.6 ppm.…”

Section: Synthesismentioning

confidence: 99%

“…All compounds were synthesized upon the reaction of the appropriate parent p-pyridine amidoxime 1 [58], ethanone oxime 14 [59] and aldoxime 21 [60] with the corresponding isocyanates 2-7 in good to excellent yields (Scheme 1). All carbamates are new, besides compound 23 [61]. For each compound, all spectroscopic and other data were collected in order to establish identity.…”

Section: Synthesis Of Carbamatesmentioning

confidence: 99%

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p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

Gritzapis

Varras

Andreou

et al. 2020

Beilstein J. Org. Chem.

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A number of p-pyridinyl oxime carbamate derivatives were prepared upon the reaction of the corresponding oximes with isocyanates. These novel compounds reacted photochemically in the presence of supercoiled plasmid DNA. Structure–activity relationship (SAR) studies revealed that the substituent on the imine group was not affecting the extend of the DNA damage, whereas the substituent of the carbamate group was critical, with the halogenated derivatives to be able to cause extensive single and double stranded DNA cleavages, acting as “synthetic nucleases”, independently of oxygen and pH. Calf thymus–DNA affinity studies showed a good-to-excellent affinity of selected both active and non-active derivatives. Preliminary theoretical studies were performed, in an effort to explain the reasons why some derivatives cause photocleavage and some others not, which were experimentally verified using triplet state activators and quenchers. These theoretical studies seem to allow the prediction of the activity of derivatives able to pass intersystem crossing to their triplet energy state and thus create radicals able to damage DNA. With this study, it is shown that oxime carbamate derivatives have the potential to act as novel effective photobase generating DNA-photocleavers, and are proposed as new leads for “on demand” biotechnological applications in drug discovery and medicine.

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