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Bis-pyrimidine acetamides: design, synthesis and biological evaluation.

Chemistry Central journal

Kumar S, Lim SM, Ramasamy K, Vasudevan M, Shah SAA, Narasimhan B.
PMID: 29086907
Chem Cent J. 2017 Aug 08;11(1):80. doi: 10.1186/s13065-017-0312-2.

BACKGROUND: In the past few years, increased resistance of microorganisms towards antimicrobial agents become a serious health problem, so there is a need for the discovery of new antimicrobial agents. On the other hand, bis-pyrimidines possess various types of...

A facile deprotection of secondary acetamides.

Organic letters

Koenig SG, Vandenbossche CP, Zhao H, Mousaw P, Singh SP, Bakale RP.
PMID: 19128192
Org Lett. 2009 Jan 15;11(2):433-6. doi: 10.1021/ol802482d.

Imidoyl chlorides, generated from secondary acetamides and oxalyl chloride, can be harnessed for a selective and practical deprotection sequence. Treatment of these intermediates with 2 equiv of propylene glycol and warming enables the rapid release of amine hydrochloride salts...

N-(4-Chloro-phenyl-sulfon-yl)-2,2,2-tri-methyl-acetamide.

Acta crystallographica. Section E, Structure reports online

Gowda BT, Foro S, Sowmya BP, Nirmala PG, Fuess H.
PMID: 21202911
Acta Crystallogr Sect E Struct Rep Online. 2008 Jun 19;64:o1279. doi: 10.1107/S1600536808017583.

In the crystal structure of the title compound (N4CPSTMAA), C(11)H(14)ClNO(3)S, the conformations of the N-H and C=O bonds in the amide group are anti to each other, similar to those observed in N-phenyl-sulfonyl-2,2,2-trimethyl-acetamide (NPSTMAA) and 2,2,2-trimethyl-N-(4-methyl-phenyl-sulfon-yl)acetamide (N4MPSTMAA). The bond...

A domino synthesis of benzoquinolinamide in the presence of iodine.

Organic & biomolecular chemistry

Zeng LY, Cai C.
PMID: 20820665
Org Biomol Chem. 2010 Nov 07;8(21):4803-5. doi: 10.1039/c0ob00364f. Epub 2010 Sep 06.

The domino synthesis of benzo[f]quinolinyl and benzo[h]quinolinyl acetamides from diketene, amines, aromatic aldehydes and naphthalenamine was developed, and the catalyst iodine was found to be crucial to the reaction. The structure was deduced from the mass spectrum, (1)H NMR,...

Radical and Heck cyclizations of diastereomeric o-haloanilide atropisomers.

Journal of the American Chemical Society

Guthrie DB, Geib SJ, Curran DP.
PMID: 21142031
J Am Chem Soc. 2011 Jan 12;133(1):115-22. doi: 10.1021/ja108795x. Epub 2010 Dec 10.

The outcomes of radical cyclizations and Heck reactions of N-(cyclohex-2-enyl)-N-(2-iodophenyl)acetamides depend critically on the configurations of the chiral axis and the stereocenter. In substrates without an ortho-methyl group, the diastereomeric precursors interconvert slowly at ambient temperatures. Cyclization of enriched...

Fine-tuning alkyne cycloadditions: Insights into photochemistry responsible for the double-strand DNA cleavage via structural perturbations in diaryl alkyne conjugates.

Beilstein journal of organic chemistry

Yang WY, Marrone SA, Minors N, Zorio DA, Alabugin IV.
PMID: 21804877
Beilstein J Org Chem. 2011;7:813-23. doi: 10.3762/bjoc.7.93. Epub 2011 Jun 16.

Hybrid molecules combining photoactivated aryl acetylenes and a dicationic lysine moiety cause the most efficient double-strand (ds) DNA cleavage known to date for a small molecule. In order to test the connection between the alkylating ability and the DNA-damaging...

Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides.

Beilstein journal of organic chemistry

Liu WB, Chen C, Zhang Q, Zhu ZB.
PMID: 22509203
Beilstein J Org Chem. 2012;8:344-8. doi: 10.3762/bjoc.8.38. Epub 2012 Mar 07.

A novel and reliable method for the direct preparation of 2,2-dihalo-N-phenylacetamides is reported. The key transformation involves the cleavage of a carbon-carbon bond in the presence of DIB and a Lewis acid as the halogen source, and thus this...

Substituted 2-[(2-Oxo-2H-[1,2,4]triazino [2,3-c]quinazolin-6-yl)thio]acetamides with Thiazole and Thiadiazole Fragments: Synthesis, Physicochemical Properties, Cytotoxicity, and Anticancer Activity.

Scientia pharmaceutica

Kovalenko SI, Nosulenko IS, Voskoboynik AY, Berest GG, Antypenko LN, Antypenko AN, Katsev AM.
PMID: 23264935
Sci Pharm. 2012 Oct-Dec;80(4):837-65. doi: 10.3797/scipharm.1208-07. Epub 2012 Oct 04.

The series of novel N-R-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazolin-6-yl)thio]acetamides with thiazole and thiadiazole fragments in a molecule were obtained by alkylation of potassium salts 1.1-1.4 by N-hetaryl-2-chloroacetamides and by aminolysis of activated acids 2.1-2.4 with N,N'-carbonyldiimidazole (CDI). The structures of compounds were determined...

Synthesis and biological evaluation of Schiff bases and azetidinones of 1-naphthol.

Journal of pharmacy & bioallied sciences

Kumar S, Kumar P, Sati N.
PMID: 22923968
J Pharm Bioallied Sci. 2012 Jul;4(3):246-9. doi: 10.4103/0975-7406.99066.

INTRODUCTION: Schiff bases and azetidinones form an important structural class possessing wide spectrum of biological activities that include antibacterial and antifungal activity. A series of Schiff's bases N'-(substituted benzylidene)-2-(naphthalen-1-yloxy) acetohydrazides (3a-f) and azetidinones N-[3-chloro-2-oxo-4-(substituted phenyl)-azetidin-1-yl]-2-(naphthalen-1-yloxy) acetamides (4a-b) were synthesized...

Recognition of N-alkyl and N-aryl acetamides by N-alkyl ammonium resorcinarene chlorides.

Chemistry (Weinheim an der Bergstrasse, Germany)

Beyeh NK, Ala-Korpi A, Cetina M, Valkonen A, Rissanen K.
PMID: 25257765
Chemistry. 2014 Nov 10;20(46):15144-50. doi: 10.1002/chem.201402533. Epub 2014 Sep 26.

N-alkyl ammonium resorcinarene chlorides are stabilized by an intricate array of intra- and intermolecular hydrogen bonds that leads to cavitand-like structures. Depending on the upper-rim substituents, self-inclusion was observed in solution and in the solid state. The self-inclusion can...

Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group.

Angewandte Chemie (International ed. in English)

Tian D, Li C, Gu G, Peng H, Zhang X, Tang W.
PMID: 29687594
Angew Chem Int Ed Engl. 2018 Jun 11;57(24):7176-7180. doi: 10.1002/anie.201712829. Epub 2018 May 09.

Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition-metal-free coupling between chiral α-aryl-α-mesylated acetamides and arylboronic acids provided access to a series of chiral α,α-diaryl acetamides with excellent enantioselectivity and moderate to...

Pd-catalyzed asymmetric allylic substitution cascade using α-(pyridin-1-yl)-acetamides formed .

Chemical science

Yao K, Yuan Q, Qu X, Liu Y, Liu D, Zhang W.
PMID: 30842843
Chem Sci. 2018 Dec 04;10(6):1767-1772. doi: 10.1039/c8sc04626c. eCollection 2019 Feb 14.

A Pd-catalyzed asymmetric allylic substitution cascade reaction, using α-(pyridin-1-yl)-acetamides (formed

Showing 1 to 12 of 115 entries