7150-57-4

Usage

Formation

Result of the reaction between 1-(2-naphthyl)-1-ethanone and phenylhydrazine

Physical State

Yellow crystalline compound

Usage

Organic synthesis and chemical research

Field of Application

Analytical chemistry

Properties

Exhibits antioxidant and antimicrobial properties

Potential Applications

Pharmaceutical and agricultural industries

Additional Use

Reagent in various chemical reactions

Significance

Valuable compound in the field of organic chemistry

InChI:InChI=1/C18H16N2/c1-14(19-20-18-9-3-2-4-10-18)16-12-11-15-7-5-6-8-17(15)13-16/h2-13,20H,1H3

Upstream product

• 59-88-1 phenylhydrazine hydrochloride 
• 93-08-3 methyl 2-naphthyl ketone 
• 100-63-0 phenylhydrazine 

Downstream Products

• 93-08-3 methyl 2-naphthyl ketone 
• 114998-79-7 2-[2]naphthyl-indol-3-one-(O-benzoyl oxime ) 

Relevant academic research and scientific papers

B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions

An efficient B(C6F5)3-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.

An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives

We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is

Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors

The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.

Novel carboxamide compound and compositions for preventing or treating metabolic diseases comprising the same

The present invention relates to a novel carboxamide compound and a composition for preventing or treating metabolic diseases comprising the same, wherein the composition is potent and selective estrogen related receptor (Estrogen-related receptor). ERR)

Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.

Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors

Oxidative stress is one of the main causes of significant severe diseases. The discovery of new potent antioxidants with high efficiency and low toxicity is a great demand in the field of medicinal chemistry. Herein, we report the design, synthesis molecu

A carboxymethyl alkyl [...] structure of 1, 3 - diaryl pyrazoles PTP1B inhibitor and its preparation and use

The present invention provides a novel carboxymethyl alkyl [...] structure of 1, 3 - diaryl pyrazole compound or its pharmaceutically acceptable salt as a novel protein tyrosine phosphatase 1 B (PTP1B) inhibitors. Studies show that this kind of inhibitor can effectively inhibit PTP1B activity, can be used as an insulin sensitizer, used for the prevention and/or treatment of PTP1B-mediated insulin resistance related diseases, in particular II type diabetes and obesity. The invention also provides a preparation method for this class of inhibitors.

Discovery of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups as potential PTP1B inhibitors

Two series of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, IIIv was found to have the best in vitro inhibition activity against PTP1B (IC50 = 0.67 ± 0.09 μM) and the best selectivity (9-fold) between PTP1B and T-cell protein tyrosine phosphatase (TCPTP). Molecular docking studies demonstrated that compounds IIIm, IIIv and IVg could occupy simultaneously at both the catalytic site and the adjacent pTyr binding site. These results provide novel lead compounds for the design of inhibitors of PTP1B as well as other PTPs.

Synthesis of some hippuric acid substrate linked novel pyrazoles as antimicrobial agents

Escalating resistance of microorganisms to the currently accessible antimicrobial drugs has forced to synthesize some novel biologically active compounds as efficient alternates via economical substrates. Hence, hippuric acid was used as one of the starting materials to synthesize pyrazole derivatives. All the synthesized compounds were characterized by IR, NMR (1H & 13C) and mass spectral data. The antimicrobial potential of synthesized compounds has been explored against four bacterial and two fungal strains. Among the 12 compounds, 3 compounds 8j, 8k and 8l were found to exhibit prominent antimicrobial potential as compared with the standards ciprofloxacin and amphotericin-B.

Novel acetohydrazide pyrazole derivatives: Design, synthesis, characterization and antimicrobial activity

Eleven acetohydrazide linked pyrazole derivatives were designed and synthesized via condensation of acetohyadrazide with different substituted formyl pyrazole derivatives under mild reaction conditions. Synthesized compounds were characterized on the basis of IR, NMR (1H & 13C) and mass spectrometry. The antimicrobial activities of all the compounds were screened against four bacterial and two fungal strains. Among the synthesized compounds, three compounds viz. 6b, 6c and 6d were found as efficient antimicrobial agents in reference to the standard drugs viz. ciprofloxacin and amphotericin-B. Further, structure-activity relationship (SAR) study revealed that electron-withdrawing group enhances the antimicrobial potential of synthesized derivatives as compared to other groups present in the ring. Hence, among compounds 6b-c, compound 6d could be explored further against other microbes to prove its vitality.