137596-49-7Relevant academic research and scientific papers
Induced fit conformational changes of a "reversed amidine" heterocycle: Optimized interactions in a DNA minor groove complex
Munde, Manoj,Lee, Michael,Neidle, Stephen,Arafa, Reem,Boykin, David W.,Liu, Yang,Bailly, Christian,Wilson, W. David
, p. 5688 - 5698 (2007)
To better understand the molecular basis for recognition of the DNA minor groove by heterocyclic cations, a series of "reversed amidine" substituted heterocycles has been prepared. Amidine derivatives for targeting the minor groove have the amidine carbon
Novel Catechol Derivatives of Arylimidamides as Antileishmanial Agents
Rezaei, Foroogh,Saghaie, Lotfollah,Sabet, Razieh,Fassihi, Afshin,Hatam, Gholamreza
, (2018/10/02)
Two novel bis-arylimidamide derivatives with terminal catechol moieties (9a and 10a) and two parent compounds with terminal phenyl groups (DB613 and DB884) were synthesized as dihydrobromide salts (9b and 10b). The designed compounds were hybrid molecules
Synthesis of dicationic 2,5-diarylpyrroles
Arafa, Reem K.,Brun, Reto,Werbovetz, Karl A.,Tanious, Farial A.,David Wilson,Boykin, David W.
, p. 423 - 428 (2007/10/03)
A new series of dicationic reversed amidine derivatives 4a-f and a substituted guanidine analog 7 of 2,5-diarylpyrrole obtained starting from the corresponding 2,5-bis(aminoaryl)pyrroles 3a-c are reported. The results of DNA binding studies and antimicrob
Models for intramolecular exchange in organic π-conjugated open-shell systems: 3-Nitrenophenyl and 4-nitrenophenyl units connected by 2,5-furandiyl, 2,5-thiophenediyl, and 2,5-pyrrolediyl nonalternant exchange linkers
Ling, Chris,Lahti, Paul M.
, p. 8784 - 8792 (2007/10/02)
The first bis(arylnitrenes) linked by heterocyclic pseudoaromatic rings were generated in a glassy, 77 K 2-methyltetrahydrofuran matrix by photolysis at wavelengths >300 nm: 2,5-bis(3-nitrenophenyl)furan (1); 2,5-bis-(3-nitrenophenyl)thiophene (2); 2,5-bi
Intermediates in the Paal-Knorr Synthesis of Pyrroles
Amarnath, Venkataraman,Anthony, Douglas C.,Amarnath, Kalyani,Valentine, William M.,Wetterau, Lawrence A.,Graham, Doyle G.
, p. 6924 - 6931 (2007/10/02)
The mechanism of Paal-Knorr reaction between a 1,4-dicarbonyl compound and ammonia or a primary amine to form a pyrrole is explored.In aprotic solvents and in aqueous solutions near neutrality, d,l diastereomers of 3,4-dimethyl- and 3,4-diethyl-2,5-hexanediones (1r and 2r) formed pyrroles 1.3-57.0 times faster than the corresponding meso diastereomers (1m and 2m).This contradicts any intermediate, such as the enamine 15, which does not remain saturated at both the 3- and 4-positions through the rate-determining step.The demonstrated stereoisomeric difference in reactivity coupled with the following results support the hemiaminal (9) as the intermediate undergoing cyclization in the rate-limiting step of the Paal-Knorr reaction: (1) The reaction rate was adversely affected by increase in the size of the alkyl substituents on the dione. (2) Racemic 2,3-dimethyl-1,4-diphenyl-1,4-butanedione (3r) was more reactive toward ammonium acetate (2.2:1) and 2-aminoethanol (11.2:1) than the meso isomer (3m), ruling out the involvement of the less substituted enamine 14. (3) The relative rate of pyrrole formation of 1,4-diphenyl-1,4-butanedione (5) and its dimethoxy (6) and dinitro (7) derivatives (1:0.3:6) does not support cyclization of the imine (11) to the pyrrolinium ion (12). (4) The rates of reaction of 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione (5D) and perdeuterio-2,5-hexanedione (4D) were very close to those of unlabeled diketones, indicating the absence of a primary isotope effect in the reaction. (5) Neither the isomerization of the unreacted diastereomers of 1, 2, and 3 nor hydrogen exchange of 4D and 5D was detected during the reaction.
