6465-03-8

Usage

InChI:InChI=1/C20H20N2O3S/c1-13(2)25-18-14(8-7-11-16(18)24-3)12-17-19(23)22-20(26-17)21-15-9-5-4-6-10-15/h4-13H,1-3H3,(H,21,22,23)

Upstream product

• 67-56-1 methanol 
• 100-25-4 para-dinitrobenzene 
• 201230-82-2 carbon monoxide 
• 100-01-6 4-nitro-aniline 
• 71026-66-9 N-(tert-butoxycarbonyl)-1,4-phenylenediamine 
• 1430115-43-7 1-Boc-methyl 4-aminophenylcarbamate 
• 100-28-7 4-Nitrophenyl isocyanate 
• 2603-10-3 N-phenyl methyl carbamate 
• 222400-05-7 methyl N-(p-nitrosophenyl)carbamate 
• 79-22-1 methyl chloroformate 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 1943-87-9 methyl N-(4-nitrophenyl)carbamate 

Downstream Products

• 1309945-86-5 C₂₀H₂₀N₄O₄ 
• 1430115-44-8 methyl 4-formamidophenylcarbamate 
• 1094106-63-4 [4-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)phenyl]carbamic acid methyl ester 
• 1430562-68-7 C₃₉H₃₇ClFN₉O₅ 
• 1430115-42-6 methyl 4-isocyanophenylcarbamate 
• 1224596-16-0 C₁₈H₁₈N₄O₄ 

Relevant academic research and scientific papers

Discovery and Structure-Based Optimization of 2-Ureidothiophene-3-carboxylic Acids as Dual Bacterial RNA Polymerase and Viral Reverse Transcriptase Inhibitors

We are concerned with the development of novel anti-infectives with dual antibacterial and antiretroviral activities for MRSA/HIV-1 co-infection. To achieve this goal, we exploited for the first time the mechanistic function similarity between the bacterial RNA polymerase (RNAP) "switch region" and the viral non-nucleoside reverse transcriptase inhibitor (NNRTI) binding site. Starting from our previously discovered RNAP inhibitors, we managed to develop potent RT inhibitors effective against several resistant HIV-1 strains with maintained or enhanced RNAP inhibitory properties following a structure-based design approach. A quantitative structure-activity relationship (QSAR) analysis revealed distinct molecular features necessary for RT inhibition. Furthermore, mode of action (MoA) studies revealed that these compounds inhibit RT noncompetitively, through a new mechanism via closing of the RT clamp. In addition, the novel RNAP/RT inhibitors are characterized by a potent antibacterial activity against S. aureus and in cellulo antiretroviral activity against NNRTI-resistant strains. In HeLa and HEK 293 cells, the compounds showed only marginal cytotoxicity.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of Formulas I-VI, including pharmaceutically acceptable salts thereof, and compositions and methods for treating human immunodeficiency virus (HIV) infection are set forth. Formula I is exemplified below: Formula (i)

SUBSTITUTED TETRAHYDROISOQUINOLINE COMPOUNDS AS FACTOR XIA INHIBITORS

The present invention provides compounds of Formula (I): or stereoisomers, pharmaceutically acceptable salts thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of factor XIa and/or plasma kallikrein which may be used as medicaments.

SUBSTITUTED TETRAHYDROISOQUINOLINE COMPOUNDS AS FACTOR XIA INHIBITORS

The present invention provides compounds of Formula (I) or stereoisomers, pharmaceutically acceptable salts thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of factor XIa and/or plasma kallikrein which may be used as medicaments.

SUBSTITUTED TETRAHYDROISOQUINOLINE COMPOUNDS AS FACTOR XIA INHIBITORS

The present invention provides compounds of Formula (I): or stereoisomers, pharmaceutically acceptable salts thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of factor XIa and/or plasma kallikrein which may be used as medicaments.

Synthesis and structure-activity relationships of (aryloxy)quinazoline ureas as novel, potent, and selective vascular endothelial growth factor receptor-2 inhibitors

In our continuing search for medicinal agents to treat proliferative diseases, quinazoline derivatives were synthesized and evaluated pharmacologically as epithelial growth factor receptor and vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase inhibitors. A quantitative structure-activity relationship analysis was conducted to rationalize the structure-activity relationship and to predict how similar the inhibitor-binding profiles of two protein kinases are likely to be on the basis of the docking of lead coumpounds into the ATP-binding site. This model was used to direct the synthesis of new compounds. A series of N-(aromatic)-N′-{4-[(6,7- dimethoxyquinazolin-4-yl)oxy]phenyl}urea were identified as potent and selective inhibitors of the tyrosine kinase activity of VEGFR-2 (fetal liver kinase 1, kinase insert domain-containing receptor). An efficient route was developed that enabled the synthesis of a wide variety of analogues with substitution on several positions of the template. Substitution of diarylurea, competitive with ATP, afforded several analogues with low nanomolar inhibition of enzymatic activity of VEGFR-2. In this paper, we describe the synthesis, structure-activity relationships, and pharmacological characterization of the series.

Novel and efficient one-pot synthesis of (aminophenyl)carbamic acid esters

A novel and efficient protocol is developed for the synthesis of various (aminophenyl) carbamic acid esters from the reduction and condensation of nitrophenyl isocyanate derivatives. The reaction takes place in various hydroxy derivatives such as alcohols or phenols under a hydrogen atmosphere using Raney nickel as catalyst. Products are obtained by a convenient one-pot synthesis with excellent yields and short reaction times.

Synthesis of alkyl N-(C-nitrosoaryl)carbamates and some reactions thereof

Reactions of alkyl N-phenylcarbamates, m-di(methoxycarboxyamido)benzene, and methyl N-(o-tolyl)carbamate with nitrosylsulfuric acid in glacial acetic acid afford N-(C-nitrosoaryl)carbamates; under these conditions tert-bulyl N-phenylcarbamate suffers decarboxylation, methyl N-(p-tolyl)-, methyl N-(p-methoxyphenyl)carbamates, o-and p-di(methoxycarboxyamido)benzenes are nitrated, and isomeric methyl N-nitrophenylcarbamates and methyl N-(p-bromophenyl)carbamate do not react. The reduction of N-(C-nitrosoaryl)carbamates with dithionite afforded the corresponding aminocarbamates; the oxidation with nitric acid yielded carbamate nitro derivatives; the condensation with aniline and benzylpyridinium chloride resulted in carbamate derivatives of azobenzene and phenylnitron.

Synthesis of some new 7-chloro-4-substituted quinolines as potential antiparasitic agents. I

The synthesis of 7-chloro-4-(substituted phenoxyquinolines, 7-chloro-4-(substituted phenylamino)quinolines and 7-chloro-4-(4-substituted phenylthio and sulfonyl)quinolines and 1-(7-chloroquinolin-4-yl)-4-substituted-piperazines has been carried out starting from 4,7-dichloroquinoline. The compounds were tested for their antimalarial activity against Plasmodium berghei in mice, antihookworm activity against Ancylostoma cylanicum in hamsters and anticestode activity against Hymenolepis nana in rats but none of them showed significant activity. When tested against Litomosoides carinii infection in cotton rats, two of the substituted piperazine compounds led to a 100% reduction of microfilariae in blood at an i.p. dose of 30 mg/kg given for 6 days.