52289-06-2

Usage

InChI:InChI=1/C9H13N3O2/c10-6-1-7-11-8-2-4-9(5-3-8)12(13)14/h2-5,11H,1,6-7,10H2

Upstream product

• 100-00-5 4-chlorobenzonitrile 
• 109-76-2 Trimethylenediamine 
• 5003-71-4 3-bromopropylamine hydrochloride 
• 100-01-6 4-nitro-aniline 
• 636-98-6 p-nitrobenzene iodide 
• 350-46-9 4-Fluoronitrobenzene 

Downstream Products

• 224313-98-8 N-(2,2-dimethyl)propionyl-N'-(p-nitrophenyl)trimethylenediamine 
• 337324-99-9 C₁₆H₂₃N₃O₃ 
• 327050-70-4 C₁₆H₁₆FN₃O₃ 
• 347356-33-6 C₁₁H₁₅N₃O₃ 
• 428849-16-5 C₁₁H₁₂F₃N₃O₃ 
• 1338494-35-1 C₁₈H₁₇ClFN₃O₄ 
• 895758-74-4 C₁₃H₁₆ClN₃O₄ 
• 1338494-37-3 C₁₆H₁₈ClN₃O₄ 
• 1338494-34-0 C₁₈H₂₄ClN₃O₄ 
• 610263-01-9 C₁₃H₁₃ClF₃N₃O₄ 
• 1352656-01-9 C₁₄H₁₇N₃O₃ 
• 187149-89-9 1-(4-Nitro-phenyl)-1,4,5,6-tetrahydro-pyrimidine 
• 224314-08-3 2-tert-butyl-1-(4-nitro-phenyl)-1,4,5,6-tetrahydro-pyrimidine 
• 775578-63-7 N-(4-nitrophenyl)propylenediamine-N',N'-diacetic acid 

Relevant academic research and scientific papers

Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine-3-carboxamide derivatives

We report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against drug-sensitive/resistant MTB strains, and they have acceptable safety indices against MTB H37Rv with the SI values of 4395 and 1405, respectively. Moreover, N-[2-(piperazin-1-yl)ethyl] moiety was also identified as a potentially alternative linker (compound 31), opening a new direction for further SAR studies.

Copper-catalyzed C-N cross-coupling reactions for the preparation of aryl diamines applying mild conditions

In this work, aryl diamines were prepared by C-N cross-coupling reactions between aryl halides and ethylenediamine. These reactions were successfully catalyzed by low quantities of Cu2O or CuO (1 mol %) employing low reflux temperature and low diamine excess. Products were afforded in good yields (up to 95%).

Potent and selective inhibitors of glutathione S-transferase omega 1 that impair cancer drug resistance

Glutathione S-transferases (GSTs) are a superfamily of enzymes that conjugate glutathione to a wide variety of both exogenous and endogenous compounds for biotransformation and/or removal. Glutathione S-tranferase omega 1 (GSTO1) is highly expressed in human cancer cells, where it has been suggested to play a role in detoxification of chemotherapeutic agents. Selective inhibitors of GSTO1 are, however, required to test the role that this enzyme plays in cancer and other (patho)physiological processes. With this goal in mind, we performed a fluorescence polarization activity-based protein profiling (fluopol-ABPP) high-throughput screen (HTS) with GSTO1 and the Molecular Libraries Small Molecule Repository (MLSMR) 300K+ compound library. This screen identified a class of selective and irreversible α-chloroacetamide inhibitors of GSTO1, which were optimized to generate an agent KT53 that inactivates GSTO1 with excellent in vitro (IC50 = 21 nM) and in situ (IC50 = 35 nM) potency. Cancer cells treated with KT53 show heightened sensitivity to the cytotoxic effects of cisplatin, supporting a role for GSTO1 in chemotherapy resistance.

Structure-activity relationship of quinoline derivatives as potent and selective α2c-adrenoceptor antagonists

Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human α2- adrenoceptor subtypes (α2A, α2B, and α2C). A number of compounds with good antagonist potencies against the α2C-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl)phenylamino]quinolin-3-yl}methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the α2c-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the α2C- adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

Thermodynamics of binding between α- and β-cyclodextrins and some p-nitro-aniline derivatives: Reconsidering the enthalpy-entropy compensation effect

The thermodynamics of binding between native α- and β-cyclodextrin towards several p-nitro-aniline derivatives was examined, in order to gain further insights about the occurrence of different interaction modes for the two hosts. Valuable information was

Design and synthesis of new ethylenediamine or propylenediamine diacetic acid derivatives for Re(I) organometallic chemistry

A general synthetic approach for a novel range of bifunctional chelating agent (BCA) for the 'fac-[M(CO)3]+' core (M= 99mTc, 99Tc or Re) has been developed. The strategy includes the facile preparation of these tridentate ligands possessing a tertiary amine bearing two carboxylic acid functions as coordinating site and an aromatic amino group for coupling to a biovector. First complexation study has shown that these compounds act exclusively as tridentate ligands (via the two acids and the tertiary amine functions). The convenient synthesis of these new ligands coupled with their high affinity for Re(I) make them quite promising for biomedical applications.