50850-13-0Relevant articles and documents
Effective nitration of anilides and acrylamides by tert-butyl nitrite
Ji, Yi-Fei,Yan, Hong,Jiang, Qi-Bai
, p. 2051 - 2060 (2015/03/18)
Nitro compounds are important intermediates in synthetic organic chemistry and the chemical industry. Herein, the efficient copper-catalyzed [10% Cu(NO3)2·3H2O] nitration of anilides was developed by using TBN (tert-butyl nitrite) as a nitrating reagent to give the corresponding nitro-substituted aromatic products in good to excellent yields. The use of TBN also led to the selective nitration of acrylamides at room temperature to afford only the (E) isomer of the nitration product. A series of anilides and acrylamides with a broad array of functional groups were well-tolerated by this procedure. This synthetic method has many advantages, which include inexpensive starting materials, mild reaction conditions, a fast reaction rate, and high yields. A mechanistic investigation indicates that a nitro radical, which is generated from the thermal homolysis of TBN, is involved in the two nitration processes. The efficient nitration of both anilides and acrylamides was achieved by using TBN (tert-butyl nitrite) as a metal-free nitrating reagent. This synthetic method has many advantages such as mild reaction conditions, a fast reaction rate, good to excellent yields, and a broad substrate scope. Our investigation indicates that a nitro radical is involved in the reaction mechanism.
Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-Aryl-substituted benzimidazoles
Roth, Thomas,Morningstar, Marshall L.,Boyer, Paul L.,Hughes, Stephen H.,Buckheit Jr., Robert W.,Michejda, Christopher J.
, p. 4199 - 4207 (2007/10/03)
The development of new nonnucleoside inhibitors of human immunodeficiency virus type-1 (HIV-1) reverse transcriptase (RT) active against the drug-induced mutations in RT continues to be a very important goal of AIDS research. We used a known inhibitor of HIV-1 RT, 1-(2,6- difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazole (TZB), as the lead structure for drug design with the objective of making more potent inhibitors against both wild-type (WT) and variant RTs. A series of structurally related 1,2-substituted benzimidazoles was synthesized and evaluated for their ability to inhibit in vitro polymerization by HIV-1 WT RT. A structure- activity study was carried out for the series of compounds to determine the optimum groups for substitution of the benzimidazole ring at the N1 and C2 positions. The best inhibitor, 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)- 4-methylbenzimidazole (35), has an IC50 = 200 nM against HIV-1 WT RT in an in vitro enzyme assay. Cytoprotection assays utilizing HIV-infected MT-4 cells revealed that 35 had strong antiviral activity (EC50 = 440 nM) against wild-type virus while retaining broad activity against many clinically observed HIV-1 strains resistant to nonnucleoside inhibitors. Overall, the activity of 35 against wild-type and resistant strains with amino acid substitution in RT is 4-fold or greater than that of TZB and is comparable to that of other nonnucleoside inhibitors currently undergoing clinical trials, most of which do not have the capacity to inhibit the variant forms of the enzyme.
A Convenient Synthesis of Carboxanilides from Silyl Carboxylates and Weakly Nucleophilic Anilines Using p-Trifluoromethylbenzoic Anhydride and a Catalytic Amount of Active Titanium(IV) Salt
Miyashita, Mitsutomo,Shiina, Isamu,Mukaiyama, Teruaki
, p. 1053 - 1054 (2007/10/02)
Various carboxanilides are prepared in excellent yields from nearly equimolar amounts of silyl carboxylates and the corresponding weakly nucleophilic anilines under mild conditions by using p-trifluoromethylbenzoic anhydride and a catalytic amount of active titanium(IV) salt.
