Synthetic strategies for antimetabolite analogs in our laboratory

Elgemeie, Galal H.; Mohamed-Ezzat, Reham A.

doi:10.1016/b978-0-12-821783-2.00008-x

Cited by 3 publications

(1 citation statement)

References 130 publications

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“…We have lately reported diverse synthetic methods for the preparation of heterocycles using cyanohydrazones [31][32][33]. Several derivatives of these ring structures are considered significant as antimetabolites in most biochemical reactions [34][35][36].…”

Section: Introductionmentioning

confidence: 99%

Unexpected Products of the Reaction of Cyanoacetylhydrazones of Aryl/heteryl Ketones with Hydrazine: A New Route to Aryl/Heteryl Hydrazones, X-ray Structure, and In vitro Anti-proliferative Activity Against NCI 60-cell Line Panel

2023

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A new unexpected synthetic non-catalytic method for the synthesis of novel heteryl hydrazones for basemodification of nucleoside analogs has been developed. Characterizations of the products have been performed using NMR spectroscopy and single crystal x-ray diffraction analysis. Further in vitro anti-proliferative potency of the compounds against NCI 60 cell lines has been estimated. The results indicate anti-cancer activity by the compounds against several of the cancer cell lines.

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Section: Introductionmentioning

confidence: 99%

Unexpected Products of the Reaction of Cyanoacetylhydrazones of Aryl/heteryl Ketones with Hydrazine: A New Route to Aryl/Heteryl Hydrazones, X-ray Structure, and In vitro Anti-proliferative Activity Against NCI 60-cell Line Panel

2023

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Crystal structures of three homologues with increasing ring size: 2-methoxy-4-(thiophen-2-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile, 2-methoxy-4-(thiophen-2-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile and 2-methoxy-4-(thiophen-2-yl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile

et al. 2023

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The title compounds, C15H14N2OS (1a), C16H16N2OS (1b), and C17H18N2OS (1c), form a homologous series in which the size of the saturated ring increases from six- to eight-membered (with four, five and six methylene groups respectively). For 1b and 1c, the central (CH2) n moieties are all displaced to the same side of their ring, and the CH2—CH2—CH2 angles are much wider than the standard sp 3 value; a database search indicates that these are general features of such ring systems. For 1a, the thiophene ring lies with the sulfur atom on the opposite side of the Cthiophene—Cpyridine bond to the cyano group, in contrast to 1b and 1c. For each compound, the packing may be described in terms of two `weak' C—H...N hydrogen bonds, which link the molecules to form one-dimensional (1a, 1c) or three-dimensional (1b) assemblies.

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An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide

Mohamed-Ezzat,

Elgemeie,

Jones

2024

Acta Crystallogr E Cryst Commun

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The title compound, C10H11N5O2S2, consists of an unexpected tautomer with a protonated nitrogen atom in the triazine ring and a formal exocyclic double bond C=N to the sulfonamide moiety. The ring angles at the unsubstituted nitrogen atoms are narrow, at 115.57 (12) and 115.19 (12)°, respectively, whereas the angle at the carbon atom between these N atoms is very wide, 127.97 (13)°. The interplanar angle between the two rings is 79.56 (5)°. The molecules are linked by three classical hydrogen bonds, forming a ribbon structure. There are also unusual linkages involving three short contacts (< 3 Å) from a sulfonamide oxygen atom to the C—NH—C part of a triazine ring.

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Synthetic strategies for antimetabolite analogs in our laboratory

Cited by 3 publications

References 130 publications

Unexpected Products of the Reaction of Cyanoacetylhydrazones of Aryl/heteryl Ketones with Hydrazine: A New Route to Aryl/Heteryl Hydrazones, X-ray Structure, and In vitro Anti-proliferative Activity Against NCI 60-cell Line Panel

Unexpected Products of the Reaction of Cyanoacetylhydrazones of Aryl/heteryl Ketones with Hydrazine: A New Route to Aryl/Heteryl Hydrazones, X-ray Structure, and In vitro Anti-proliferative Activity Against NCI 60-cell Line Panel

An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide

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