Nitroimidazoles Part 8. Synthesis and Anti-HIV Activity of New 4-Nitroimidazole Derivatives Using the Suzuki Cross-Coupling Reaction

2012 ◽  
Vol 67 (9) ◽  
pp. 925-934 ◽  
Author(s):  
Yaseen A. Al-Soud ◽  
Najim A. Al-Masoudi ◽  
Hossam H. Al-Suod ◽  
Christophe Pannecouque
Keyword(s):  
Methyl Esters ◽  
Coupling Reaction ◽  
Suzuki Coupling Reaction ◽  
Piperazine Derivatives ◽  
Acid Methyl ◽  
Cross Coupling Reaction ◽  
Anti Hiv ◽  
Benzamide Derivatives ◽  
Hiv 1 ◽  
Amino Acid Methyl Esters

The development of new HIV non-nucleoside reverse transcriptase inhibitors (NNRTIs) offers the possibility of generating structures of increased potency. To this end, a series of 1-(1-benzyl-2-ethyl- 4-nitro-1H-imidazol-5-yl)-4-(1,1'-biaryl)-4-yl-piperazine derivatives (6a-l) was synthesized via the Suzuki coupling reaction. Analogously, coupling of the acid derivative 5, prepared from 4, with various amino acid methyl esters in the presence of HOBt/DCC reagents afforded the benzamide derivatives 8-11. The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT- 4 cells. All compounds are inactive, except compound 6f which showed inhibition of HIV-1 with EC50 = 2:60μgmL-1 with a selectivity index (SI) of 9

New Aryl-1,3-thiazole-4-carbohydrazides, Their 1,3,4-Oxadiazole-2- thione, 1,2,4-Triazole, Isatin-3-ylidene and Carboxamide Derivatives. Synthesis and Anti-HIV Activity

2012 ◽  
Vol 67 (7) ◽  
pp. 747-758 ◽  
Author(s):  
Mehwash Zia ◽  
Tashfeen Akhtar ◽  
Shahid Hameed ◽  
Najim A. Al-Masoudi
Keyword(s):  
Amino Acid ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Anti Hiv ◽  
Hiv 1 ◽  
Amino Acid Methyl Esters

A series of isatin-3-ylidene (6a-i) and arylthiazolyl-1,3,4-oxadiazole-2-thione derivatives 7a-i derived from arylthiazolyl carbohydrazide analogs 4a-i were synthesized. Analogously, coupling of 4f with various amino acid methyl esters in the presence of HOBt/DCC reagents afforded the carboxamide derivatives 9a-d. The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. All compounds are inactive, except compounds 9b and 9c which showed inhibition of HIV-1 with EC50 = 2:34 μg mL-1, and 1.12 μg mL-1 with therapeutic indexes (SI) of 9 and <1, respectively.

Highly Stereoselective Synthesis of Optically Pure C-Aryl Imines from α-L-Amino Acid Methyl Esters.

ChemInform ◽  
2004 ◽  
Vol 35 (17) ◽  
Author(s):  
Antonella Leggio ◽  
Adolfo Le Pera ◽  
Angelo Liguori ◽  
Anna Napoli ◽  
Claudio Romeo ◽  
...  
Keyword(s):  
Amino Acid ◽  
Stereoselective Synthesis ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Optically Pure ◽  
Amino Acid Methyl Esters

ANTIMICROBIAL STUDIES OF NEWLY SYNTHESIZED 1H-BENZOTRIAZOLE-1-ACETYL-AMINO ACID METHYL ESTERS /PEPTIDE DERIVATIVES

INDIAN DRUGS ◽  
2013 ◽  
Vol 50 (12) ◽  
pp. 27-33
Author(s):  
K. Kaur ◽  
◽  
R Kaur ◽  
A. Kaur
Keyword(s):  
Amino Acid ◽  
1H Nmr Spectroscopy ◽  
Methyl Esters ◽  
Penicillium Expansum ◽  
Antimicrobial Compounds ◽  
Bacterial Strains ◽  
Antimicrobial Studies ◽  
Acid Methyl ◽  
Peptide Derivatives ◽  
Amino Acid Methyl Esters

Benzotriazole-1-acetic acid was coupled with amino acid methyl esters/ dipeptides/ tripeptides/tetrapeptides in the presence of DCC as a coupling agent and NMM as a base under continuous stirringfor 36 hrs. The reactions were monitored by TLC. The newly synthesized compounds were analyzedand the structures were confirmed by IR and 1H NMR spectroscopy. The synthesized compounds weretested against bacterial strains Bacillus subtilis, Staphylococcus aureus and Escherichia coli by usingciprofloxacin as standard in the concentration of 20?g/mL. All the compounds were also tested againstfungal strains Candida albicans, Aspergillus niger and Penicillium expansum by using fluconazole asstandard in the concentration of 10?g/mL. Compounds 1, 2, 3 and 4 were found to be more potent antimicrobial compounds.

Multifunctional lubricant additives derived from natural amino acids and methyl oleate

RSC Advances ◽  
2015 ◽  
Vol 5 (95) ◽  
pp. 77538-77544 ◽  
Author(s):  
Arukali Sammaiah ◽  
Korlipara V. Padmaja ◽  
Shiva Shanker Kaki ◽  
Rachapudi B. N. Prasad
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Oleate ◽  
Thioglycolic Acid ◽  
Methyl Esters ◽  
Lubricant Additives ◽  
Acid Methyl ◽  
Multifunctional Additives ◽  
Natural Amino Acids ◽  
Amino Acid Methyl Esters

Novel multifunctional additives were synthesized from methyl oleate via thioglycolic acid addition followed by condensation with different amino acid methyl esters.

One-pot synthesis of 4-arylidene imidazolin-5-ones by reaction of amino acid esters with isocyanates and α-bromoketones

2019 ◽  
Vol 17 (11) ◽  
pp. 3040-3047
Author(s):  
Jia-Yun Haung ◽  
Indrajeet J. Barve ◽  
Chung-Ming Sun
Keyword(s):  
Amino Acid ◽  
Multicomponent Reaction ◽  
Methyl Esters ◽  
Amino Acid Esters ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Methyl ◽  
Acid Esters ◽  
Amino Acid Methyl Esters

A one-pot multicomponent reaction for assembling substituted 4-arylidene imidazolin-5-ones from l-amino acid methyl esters, iso-, isothio- or isoselenocyanates, and α-bromoketones has been discovered.

Syntheses of 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of 2-substituted-5-fluoroaniline: "cytosine replacement" analogs of deoxycytidine for evaluation as anticancer and antihuman immunodeficiency virus (anti-HIV) agents

2000 ◽  
Vol 78 (8) ◽  
pp. 1081-1088
Author(s):  
Zhi-Xian Wang ◽  
Leonard I Wiebe ◽  
Erik De Clercq ◽  
Jan Balzarini ◽  
Edward E Knaus
Keyword(s):  
Anticancer Agent ◽  
Coupling Reaction ◽  
Tumor Cell Lines ◽  
Immunodeficiency Virus ◽  
Sugar Ring ◽  
Type Coupling ◽  
Anti Hiv Agents ◽  
Derivatives Of ◽  
Anti Hiv ◽  
Hiv 1

A group of 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of 5-fluoroaniline possessing a variety of aryl C-2 substituents (6a R = H, 6b R = F, 6c R = Me) were synthesized. Accordingly, a Heck-type coupling reaction of the 4-iodoaniline derivatives (13a–c) with the bis(tert-butyldimethylsilyl)glycal (11) in the presence of Pd(OAc)2 and Ph3As, followed by removal of the tert-butyldimethylsilyl protection groups using n-Bu4N+F-, yielded the corresponding 4-(β-D-glycero-pentofuran-3-ulos-1-yl)aniline derivatives (14a–c) having a C-3 C=O in the sugar ring. Reduction of the C-3 C=O compounds (14a–c) using NaB(OAc)3H afforded the target 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of the respective 2-substituted-5-fluoroaniline (6a–c). The deoxycytidine mimic, 3-fluoro-4-[1-(2-deoxy-β-D-ribofuranosyl)]aniline (6a), in which the cytosine ring of deoxycytidine is replaced by a 4-(3-fluoroaniline) ring system, was inactive as an anticancer agent against a variety of tumor cell lines, and as an antihuman immunodeficiency virus (HIV-1, HIV-2) agent. The failure of this unnatural deoxycytidine mimic (6a) to exhibit anticancer-antiviral activity may be due to its inability to undergo phosphorylation by host cell- and virus-induced kinases.Key words: fluoroanilines, deoxycytidine mimics, anticancer-antihuman immunodeficiency virus (HIV) evaluation.

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