2016
DOI: 10.1002/chem.201600308
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One‐Step Synthetic Access to Isosteric and Potent Anticancer Nitrogen Heterocycles with the Benzo[c]phenanthridine Scaffold

Abstract: A versatile one-step two-component cyclization to build new tetracyclic nitrogen heterocycles is described. Ortho-methylhetarenecarbonitrile components were condensed with aldehydes to access a large library of differently substituted ring systems. The heterocyclic core can be easily modified by variation of the position of the endocyclic nitrogen atom in the o-methylhetarenecarbonitrile substrate. The manner of the nucleophilic attack that leads to the condensation can be triggered by different electron-densi… Show more

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Cited by 7 publications
(8 citation statements)
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“… Natural‐product‐inspired development of aza‐analogs of benzo[ c ]phenanthridines . R 1 =OH, R 2 =OCH 3 : fagaronine; R 1 –R 2 = OCH 2 O: nitidine; R 3 =variously substituted aryl or alkyl groups; R 4 =H, OH, NH 2 , or various hydrophilic sidechains.…”
Section: Figurementioning
confidence: 99%
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“… Natural‐product‐inspired development of aza‐analogs of benzo[ c ]phenanthridines . R 1 =OH, R 2 =OCH 3 : fagaronine; R 1 –R 2 = OCH 2 O: nitidine; R 3 =variously substituted aryl or alkyl groups; R 4 =H, OH, NH 2 , or various hydrophilic sidechains.…”
Section: Figurementioning
confidence: 99%
“…To overcome these disadvantages, we synthesized aza‐analogs of benzo[ c ]phenanthridines (compounds 9 – 14 ) by using various o ‐methylhetarene carbonitriles, and the core system was systematically adapted and optimized for both physicochemical properties and cytotoxicity (Figure ) . Applying the concept of an aminoalkyl side chain linked to a planar core system to achieve DNA intercalation as well as anti‐topoisomerase activity, the pyrido[3,4‐ c ][1,9]phenanthroline P8‐D6 ( 19 ) was found to be by far the most potent derivative of our compound library.…”
Section: Figurementioning
confidence: 99%
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“…The high variability of the substituent at position 11 along with the possibility to build up N‐containing heterocyclic structures with N‐functionalized o ‐methylheteroaryl carbonitriles underlines the broad applicability and importance of this cyclization in heterocyclic chemistry. Using the synthetic route developed in our research group, a large number of recently discovered aza‐substituted benzo[ c ]phenanthridine isosteres are accessible (Scheme ) . These are the 11‐substituted 6‐amino‐11,12‐dihydropyrido[3,2‐ c ][1,7]phenanthrolines 5 , the 11‐substituted 6‐amino‐11,12‐dihydropyrido[4,3‐ c ][1,8]phenanthrolines 6 , together with 6‐substituted 5,6‐dihydro‐11 H ‐pyrido[3,4‐ i ]‐3‐azarcarbazoles 7 , 11‐substituted 6‐amino‐11,12‐dihydropyrido[3,4‐ c ][1,9]phenanthrolines 8 , 6‐substituted 5,6‐dihydro‐11 H ‐pyrido[3,2‐ i ]‐1‐azarcarbazoles 9 , and 11‐substituted 6‐amino‐11,12‐dihydropyrido[2,3‐ c ][1,10]phenanthrolines 10 and 11‐substituted 6‐amino‐1‐aza‐11,12‐dihydropyrimido[5,4‐ c ][1,9]phenanthrolines 11 , recently derived heterocyclic ring systems, which could be readily obtained by variation of the nitrile component 1 , namely with nitriles 12 – 16 with heterofunctionalized analogous structures bearing the nitrogen atom at different positions (Scheme ) …”
Section: Introductionmentioning
confidence: 99%
“… Working the nitrogen atoms of the carbonitrile around the clock affords a plethora of hitherto unknown substituted scaffolds using Clement–Weide cyclization …”
Section: Introductionmentioning
confidence: 99%