856794-72-4

Upstream product

• 16426-64-5 2-bromo-4-nitrobenzoic acid 
• 7745-93-9 2-bromo-4-nitrotoluene 

Downstream Products

• 1240662-80-9 2-bromo-4-nitro-N-(2-phenyl-2-propyl)benzamide 
• 1283116-53-9 4-amino-N-benzyl-2-bromobenzamide 
• 1283116-55-1 (S)-4-(2-amino-4-methylpentanamido)-N-benzyl-2-bromobenzamide 
• 1283116-60-8 N-benzyl-2-bromo-4-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-benzamide 
• 1283116-64-2 N₂-benzyl-5-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-biphenyl-2,4'-dicarboxamide 
• 1283116-66-4 N-benzyl-4'-cyano-5-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-[1,1'-biphenyl]-2-carboxamide 
• 1283116-68-6 methyl 2'-(benzylcarbamoyl)-5'-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-[1,1'-biphenyl]-4-carboxylate 
• 1283116-70-0 N₂-benzyl-5-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-[1,1'-biphenyl]-2,3'-dicarboxamide 
• 1283116-72-2 N-benzyl-3'-cyano-5-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propanamido)-4-methylpentanamido)-[1,1'-biphenyl]-2-carboxamide 
• 1283116-74-4 methyl 2'-(benzylcarbamoyl)-5'-((S)-2-((S)-2-(4-cyanobenzamido)-3-(4-hydroxyphenyl)propan-amido)-4-methylpentanamido)-[1,1'-biphenyl]-3-carboxylate 
• 1283116-86-8 4-((S)-3-(((S)-1-((6-(benzylcarbamoyl)-4'-carbamoyl-[1,1'-biphenyl]-3-yl)amino)-4-methyl-1-oxopentan-2-yl)-amino)-2-(4-cyanobenzamido)-3-oxopropyl)phenyl N,N,N',N'-tetramethylphosphordiamidate 
• 1283116-87-9 4-((S)-3-(((S)-1-((6-(benzylcarbamoyl)-4'-cyano-[1,1'-biphenyl]-3-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-2-(4-cyanobenzamido)-3-oxopropyl)phenyl N,N,N',N'-tetramethylphosphordiamidate 
• 1283116-88-0 methyl 2'-(benzylcarbamoyl)-5'-((S)-2-((S)-3-(4-((bis-(dimethylamino)phosphoryl)oxy)phenyl)-2-(4-cyanobenzamido)propanamido)-4-methylpentanamido)-[1,1'-biphenyl]-4-carboxylate 
• 1283116-89-1 4-((S)-3-(((S)-1-((6-(benzylcarbamoyl)-3'-carbamoyl-[1,1'-biphenyl]-3-yl)amino)-4-methyl-1-oxopentan-2-yl)-amino)-2-(4-cyanobenzamido)-3-oxopropyl)phenyl N,N,N',N'-tetramethylphosphordiamidate 

Relevant academic research and scientific papers

Synthesis of a novel pyrrolo-benzoxaborole scaffold and its derivatization via Friedel-Crafts reaction catalyzed by anhydrous stannic chloride

A novel pyrrolo-benzoxaborole, 6-(pyrrol-1-yl)-1,3-dihydro-1-hydroxy-2,1- benzoxaborole, was synthesized with 27% overall yield over six steps from 2-bromo-1-methyl-4-nitrobenzene as starting material. Its derivatization was achieved via Friedel-Crafts re

Scope and mechanism of a true organocatalytic beckmann rearrangement with a boronic acid/perfluoropinacol system under ambient conditions

Catalytic activation of hydroxyl functionalities is of great interest for the production of pharmaceuticals and commodity chemicals. Here, 2-alkoxycarbonyl- and 2-phenoxycarbonyl-phenylboronic acid were identified as efficient catalysts for the direct and chemoselective activation of oxime N-OH bonds in the Beckmann rearrangement. This classical organic reaction provides a unique approach to prepare functionalized amide products that may be difficult to access using traditional amide coupling between carboxylic acids and amines. Using only 5 mol % of boronic acid catalyst and perfluoropinacol as an additive in a polar solvent mixture, the operationally simple protocol features mild conditions, a broad substrate scope, and a high functional group tolerance. A wide variety of diaryl, aryl-alkyl, heteroaryl-alkyl, and dialkyl oximes react under ambient conditions to afford high yields of amide products. Free alcohols, amides, carboxyesters, and many other functionalities are compatible with the reaction conditions. Investigations of the catalytic cycle revealed a novel boron-induced oxime transesterification providing an acyl oxime intermediate involved in a fully catalytic nonself-propagating Beckmann rearrangement mechanism. The acyl oxime intermediate was prepared independently and was subjected to the reaction conditions. It was found to be self-sufficient; it reacts rapidly, unimolecularly without the need for free oxime. A series of control experiments and 18O labeling studies support a true catalytic pathway involving an ionic transition structure with an active and essential role for the boronyl moiety in both steps of transesterification and rearrangement. According to 11B NMR spectroscopic studies, the additive perfluoropinacol provides a transient, electrophilic boronic ester that is thought to serve as an internal Lewis acid to activate the ortho-carboxyester and accelerate the initial, rate-limiting step of transesterification between the precatalyst and the oxime substrate.

Novel pyrrolobenzoxaboroles: Design, synthesis, and biological evaluation against Trypanosoma brucei

Human African trypanosomiasis is a fatal parasitic infection caused by the protozoan Trypanosoma brucei. The development of novel antitrypanosomal agents is urgently needed. Here we report the synthesis and structure-activity relationship of a new class of benzoxaboroles as antitrypanosomal agents. These compounds showed antiparasitic IC50 values ranging from 4.02 to 0.03 μg/mL and satisfactory cytotoxicity profile. Three of the lead compounds were demonstrated to cure the parasitic infection in a murine acute infection model. The structure-activity relationship of the pyrrolobenzoxaboroles are also discussed.

Hypervalent iodine(III)-mediated oxidative dearomatizing cyclization of arylamines

An oxidative dearomatizing cyclization of arylamines promoted by iodobenzene bis(trifluoroacetate) [PhI(CF3CO2) 2] has been explored, leading to a novel synthetic approach to functionalized spirocyclic building blocks containing the structurally unique dieniminium moiety. This unprecedented methodology, featuring oxidative dearomatization and carbon-carbon bond-forming cyclization, to some extent, not only expands the synthetic potential of hypervalent iodine chemistry, but also enriches the oxidation chemistry of arylamines.

Design, synthesis and in vitro characterization of novel hybrid peptidomimetic inhibitors of STAT3 protein

Aberrant activation of oncogenic signal transducer and activator of transcription 3 (STAT3) protein signaling pathways has been extensively implicated in human cancers. Given STAT3's prominent dysregulatory role in malignant transformation and tumorigenesis, there has been a significant effort to discover STAT3-specific inhibitors as chemical probes for defining the aberrant STAT3-mediated molecular events that support the malignant phenotype. To identify novel, STAT3-selective inhibitors suitable for interrogating STAT3 signaling in tumor cells, we explored the design of hybrid molecules by conjugating a known STAT3 inhibitory peptidomimetic, ISS610 to the high-affinity STAT3-binding peptide motif derived from the ILR/gp-130. Several hybrid molecules were examined in in vitro biophysical and biochemical studies for inhibitory potency against STAT3. Lead inhibitor 14aa was shown to strongly bind to STAT3 (KD = 900 nM), disrupt STAT3:phosphopeptide complexes (Ki = 5 μM) and suppress STAT3 activity in in vitro DNA binding activity/electrophoretic mobility shift assay (EMSA). Moreover, lead STAT3 inhibitor 14aa induced a time-dependent inhibition of constitutive STAT3 activation in v-Src transformed mouse fibroblasts (NIH3T3/v-Src), with 80% suppression of constitutively-active STAT3 at 6 h following treatment of NIH3T3/v-Src. However, STAT3 activity recovered at 24 h after treatment of cells, suggesting potential degradation of the compound. Results further showed a suppression of aberrant STAT3 activity in NIH3T3/v-Src by the treatment with compound 14aa-OH, which is the non-pTyr version of compound 14aa. The effect of compounds 14aa and 14aa-OH are accompanied by a moderate loss of cell viability.

Enantioselective synthesis of axially chiral biaryls by the pd-catalyzed suzuki-miyaura reaction: Substrate scope and quantum mechanical investigations

We report efficient syntheses of axially chiral biaryl amides in yields ranging from 80-92%, and with enantioselectivity in the range 88-94% ee employing an asymmetric Suzuki-Miyaura process with Pd(OAc)2 and KenPhos as ligand. These studies demonstrate that electron-rich and electron-deficient o-halobenzamides can be efficiently coupled with 2-methyl-1-naphthylboronic acid and 2-ethoxy-1-naphthylboronic acid. The yields and selectivities of the reactions are independent of the nature of halogen substituent on the benzamide coupling partner. Our investigations demonstrate that axially chiral heterocyclic and biphenyl compounds can also be synthesized with this methodology. We also report computational studies used to determine the origin of stereoselectivity during the selectivity-determining reductive elimination step of the related coupling of tolyl boronic acid with naphthylphosphonate bromide that was reported in a previous publication (J. Am. Chem. Soc. 2000, 122, 12051-12052). These studies indicate that the stereoselectivity arises from a combination of weak -(C)H??O interactions as well as steric interactions between the tolyl and naphthylphosphonate addends in the transition state for C-C coupling.

Cytotoxicity and TOP1-targeting activity of 8- and 9-amino derivatives of 5-butyl- and 5-(2-N,N-dimethylamino)ethyl-5H-dibenzo[c,h][1,6]naphthyridin-6-ones

Studies on substituted 5H-dibenzo[c,h][1,6]naphthyridin-6-ones and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones have demonstrated that hydrophilic substituents at the 2-position of an ethyl group at the 5- and 6-positions, respectively, can enhance biological

Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine

Syntheses of 3-substituted indazoles and benzoisoxazoles were efficiently accomplished with the aid of Pd-catalyzed intramolecular carbon-nitrogen and carbon-oxygen bond formations. The catalyst system described herein allows the cyclization to proceed under very mild conditions and thus could be applied to a wide range of substrates with acid- or base-sensitive functional groups. A total synthesis for the indazole ring-containing natural product nigellicine is also described.

NITRO AND AMINO SUBSTITUTED TOPOISOMERASE AGENTS

The invention provides compounds of formula (I): wherein R1-R9, W, and X have any of the meanings defined in the specification and their pharmaceutically acceptable salts. The invention also provides pharmaceutical compositions compr

Nitro and amino substitution in the D-ring of 5-(2-dimethylaminoethyl)2,3-methylenedioxy-5H-dibenzo[c,h][1,6] naphthyridin-6-ones: Effect on topoisomerase-I targeting activity and cytotoxicity

5H-8,9 -Dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo [c,h][1,6]naphthyridin-6-one exhibits potent TOP1-targeting activity and pronounced antitumor activity. It was hypothesized that replacement of the two methoxyl groups with a nitro s