- DNA-Encoded Libraries: Hydrazide as a Pluripotent Precursor for On-DNA Synthesis of Various Azole Derivatives
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DNA-encoded combinatorial chemical library (DEL) technology, an approach that combines the power of genetics and chemistry, has emerged as an invaluable tool in drug discovery. Skeletal diversity plays a fundamental importance in DEL applications, and relies heavily on novel DNA-compatible chemical reactions. We report herein a phylogenic chemical transformation strategy using DNA-conjugated benzoyl hydrazine as a common versatile precursor in azole chemical expansion of DELs. DNA-compatible reactions deriving from the common benzoyl hydrazine precursor showed excellent functional group tolerance with exceptional efficiency in the synthesis of various azoles, including oxadiazoles, thiadiazoles, and triazoles, under mild reaction conditions. The phylogenic chemical transformation strategy provides DELs a facile way to expand into various unique chemical spaces with privileged scaffolds and pharmacophores.
- Ma, Fei,Li, Jie,Zhang, Shuning,Gu, Yuang,Tan, Tingting,Chen, Wanting,Wang, Shuyue,Ma, Peixiang,Xu, Hongtao,Yang, Guang,Lerner, Richard A.
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supporting information
p. 8214 - 8220
(2021/05/03)
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- Colchicine derivatives, and preparation method and medical application thereof
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The invention specifically relates to colchicine derivatives (I) as described in the specification and a preparation method thereof, and pharmaceutical compositions containing the colchicine derivatives, belonging to the field of medicinal chemistry. The results of pharmacodynamic experiments prove that the colchicine derivatives of the invention have treatment effect on lumbar disc herniation andliver fibrosis.
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Paragraph 0092; 0093; 0154; 0156; 0157
(2018/09/14)
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- Synthesis of secondary amides from N-Substituted amidines by tandem oxidative rearrangement and isocyanate elimination
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In this work an efficient tandem process transforming N-substituted amidines into secondary amides has been described. The process involves N-acylurea formation by reaction of the substrate with bis(acyloxy)(phenyl)-λ3-iodane followed by isocyanate elimination. The periodinane reagents are obtained from the commercially available phenyl-iodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N-substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting of sterically hindered acids and amines. Moreover, the protocol allows one to combine steric bulk with electron deficiency in the target amides (aniline based). Such compounds are difficult to synthesize efficiently based on classical condensation reactions involving carboxylic acids and amines. Overall, the synthetic protocol transforms a nitrile into a secondary amide in both aliphatic and (hetero)aromatic systems.
- Debnath, Pradip,Baeten, Mattijs,Lefvre, Nicolas,Van Daele, Stijn,Maes, Bert U. W.
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supporting information
p. 197 - 209
(2015/03/03)
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- Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates
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Two methods for the synthesis of 3,5-diaryl-1,2,4-triazoles, both domino reactions, are reported. The first procedure, the Cu(OTf)2-catalyzed reaction between two amidines using NaHCO3 as a base, 1,10-phenanthroline as an additive and K3[Fe(CN)6]/ atmospheric oxygen as the oxidant, delivers 3,5-diaryl-1,2,4-triazoles with yields up to 68%. The second procedure for the synthesis of 3,5-diaryl-1,2,4- triazoles with yields up to 64% rests on the Cu(OTf)2-catalyzed reaction between two imidates and ammonium carbonate. This method features the formation of three bonds in a single synthetic step.
- Sudheendran, Kavitha,Schmidt, Dietmar,Frey, Wolfgang,Conrad, Jürgen,Beifuss, Uwe
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p. 1635 - 1645
(2014/02/14)
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- Synthesis and structure of aroylamidines and N-arylbenzamidines hydrochlorides
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Aroylamidines can be obtained as salts in a reaction of the corresponding arylcarbonitriles with anhydrous ethanol in the presence of dry HCl followed by treating intermediate imidoesters with alcoholic solution of ammonia. N-Arylbenzamidines are obtained by reacting benzonitrile with arylamines in the presence of AlCl3. The structure of arylamines and the reaction conditions signifi cantly affect the yield of the target product, and sometimes the very possibility of its preparation. Pleiades Publishing, Ltd., 2012.
- Kuvaeva,Fedorova,Zaitsev,Yakovlev,Zakharov,Semakova
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experimental part
p. 209 - 213
(2012/06/01)
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- Syntheses, characterization and antimicrobial activity of some substituted 1,2,4-triazole derivatives
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Syntheses of a series of 4-amino-3,5-dialkyl-1,2,4-triazoles are described. In present work, iminoester hydrochlorides (1) was treated with acyl hydrazines to obtain acylhydrazones (2). The compound acylhydrazones (2) converted to the 4-amino-3,5-dialkyl-
- Singh,Singh
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experimental part
p. 2659 - 2663
(2010/11/05)
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- Reverse-benzamidine antimalarial agents: Design, synthesis, and biological evaluation
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In the frame of the development of bis-cationic choline analogs, the RSA of bis-N-alkylamidines were studied and a new series of reverse-benzamidine derivatives was designed. Contrary to the lipophilicity, the basicity of alkylamidine compounds directly influences their antimalarial potencies.
- Berger, Olivier,Wein, Sharon,Duckert, Jean-Frederic,Maynadier, Marjorie,Fangour, Siham El,Escale, Roger,Durand, Thierry,Vial, Henri,Vo-Hoang, Yen
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experimental part
p. 5815 - 5817
(2010/11/17)
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- Synthesis, structures of some unsymmetrical 3,6-disubstituted-1,2,4,5- tetrazines
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(Chemical Equation Presented) A series of new unsymmetrical 3-phenyl-6-benzyl-1,2,4,5-tetrazine derivatives 10a-i were synthesized and characterized by IR, NMR, MS, and element analysis. The structures of 4a, 10c, 10d and 10h were analyzed by X-ray crystallography, which had intermolecular C-H...N, C-H...Cl, C-H...Π and Π...Π H interactions.
- Hu, Wei-Xiao,Xu, Feng
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scheme or table
p. 1745 - 1750
(2009/05/31)
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- EPOTHILONE ANALOGUES MODIFIED AT POSITIONS C12-C13 AS ANTICANCER DRUGS
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The invention relates to analogues of epothilones of formulae (A), (B), (I) and (II), uses and methods of making the same.
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Page/Page column 32
(2008/12/06)
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- HETEROCYCLIC AMIDE COMPOUNDS AND PHARMACEUTICAL USE OF THE SAME
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Heterocyclic amide compounds of the formula (I) STR1 wherein each symbol is as defined in the specification, pharmacologically acceptable salts thereof, pharmaceutical compositions thereof and pharmaceutical use thereof. The heterocyclic amide compounds and pharmacologically acceptable salts thereof of the present invention have superior inhibitory activity against chymase groups in mammals inclusive of human, and can be administered orally or parenterally. Therefore, they are useful as chymase inhibitors and can be effective for the prophylaxis and treatment of various diseases caused by chymase, such as those caused by angiotensin II.
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- Synthesis and Structure of Alkyl N-Acylimidates
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Alkyl N-acylimidates 1 are prepared more easily and in higher yields than before by reaction of alkyl imidate hydrochlorides 5 with acyl halides 7 in the presence of 2.2 mol of base (14 examples).The X-ray analysis of a crystalline derivative (1dbd) shows, that the C=N- and C=O parts are twisted significantly (torsional angle 77.6 deg).The stereochemical, dynamic and electronic properties of the compounds 1 are interpreted by means of ab initio 3-21 G calculations on conformers of the parent system HO-CH=N-CH=O (8).Low rotational (ca. 6 kcal/mol) and inversional (max. 8 kcal/mol) barriers indicate the many favourable electronic interactions between the C=N- and the C=O groups in such N-functionalised imine derivatives.The compound 1 are significantly higher in energy than bisacylamines and are therefore suggested to be superior, more reactive synthetic C-N-C building blocks.The spectroscopic properties (IR, 13C- and 1H NMR, MS) are given and discussed.
- Kupfer, Rainer,Nagel, Michael,Wuerthwein, Ernst-Ulrich,Allmann, Rudolf
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p. 3089 - 3104
(2007/10/02)
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