32896-98-3

Usage

InChI:InChI=1/C14H14NO.BrH/c1-12-7-5-6-10-15(12)11-14(16)13-8-3-2-4-9-13;/h2-10H,11H2,1H3;1H/q+1;/p-1

Upstream product

• 109-06-8 α-picoline 
• 70-11-1 α-bromoacetophenone 
• 98-86-2 acetophenone 

Downstream Products

• 73916-31-1 [2-furan-2-yl-5-methyl-1-(5-nitro-furan-2-yl)-indolizin-3-yl]-phenyl-methanone 
• 90650-46-7 (3aR,4R,9aS,9bS)-4-Benzoyl-6-methyl-2-p-tolyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione 
• 25379-20-8 2-phenylindolizine 
• 83260-60-0 2,3-Dipropyl-quinolizinylium; bromide 
• 131354-29-5 [1,3]Azaphospholo[1,5-a]pyridin-3-yl-phenyl-methanone 
• 16171-40-7 2,3-diphenylquinolizinium bromide 
• 83260-55-3 dibenzo[f,h]pyrido[1,2-b]isoquinolinylium; bromide 
• 49618-59-9 dimethyl 3-phenylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate 
• 49618-62-4 1,2-dicarboxy-3-phenylcycl[3.2.2]azine 

Relevant academic research and scientific papers

Dithiolation indolizine exerts viability suppression effects on A549 cells via triggering intrinsic apoptotic pathways and inducing G2/M phase arrest

Indolizine derivatives have been reported for the treatment of numerous diseases. However, few studies were carried out for non-small cell lung cancer (NSCLC). We synthesized series of indolizine compounds. The results of MTT assay showed compound 8 (C8) markedly inhibited the proliferation of A549 cells, however, C8 (15, 30 μg/mL) had little cytotoxicity in other cell lines (SH-SY5Y, HepG2, and BEAS-2B cells), Hoechst staining and JC-1 staining showed that C8 induced changes in the nucleus morphology, increased the loss in mitochondrial membrane potential in A549 cells. The results of flow cytometry manifested that cell cycle of the cells was arrested in the G2 / M phase by C8, ROS levels and the proportion of apoptosis of cells increased. We performed western blotting analysis to detect the expression levels of apoptosis and cycle-related proteins. These results validated that the apoptosis of cells was triggered by endoplasmic reticulum stress (ERS) and the PI3K/Akt-mediated mitochondrial pathway collaboratively. Besides, the utilization of PI3K/Akt inhibitors and p53 inhibitors further proves the above argument and C8-induced cycle arrest of A549 cells is majorly regulated by p53. C8 induced the accumulation of ROS contents involved in mitochondrial damage. The proliferation of A549 cells was inhibited after treatment with the compound, which induced apoptosis and cycle arrest of cells. It is suggested that C8(dithiolation indolizine) is a potential candidate compound against non-small cell lung cancer.

Synthesis of 1,2-Dicyano-3-arylcycl[3.2.2]azines – First 1,2-Dicarbonitriles Based on Cyclazine Heterocycle

The first 1,2-dicarbonitriles have been prepared for cyclazine systems. In particular, a synthetic procedure to 1,2-dicyano-3-arylcycl[3.2.2]azines has been developed. Unexpected chlorination of 3-arylcycl[3.2.2]azine-1,2-dicarboxylic acid derivatives by thionyl chloride at 4-position was found, which according to theoretical considerations can proceed by the electrophilic (SEAr) mechanism. The compounds are blue fluorophores in 450–480 nm region with quantum yields in toluene of ca. 30 % for non-chlorinated derivatives, which decrease to 3–4 % for chlorinated ones.

Acidification corrosion inhibitor based on interpolymer indolizine derivative as well as preparation method and application thereof

The invention discloses an acidification corrosion inhibitor based on an interpolymer indolizine derivative as well as a preparation method and application thereof. The acidification corrosion inhibitor contains the interpolymer indolizine derivative; the interpolymer indolizine derivative is prepared by carrying out decarboxylation on heterocyclic alkali including (substituted) quinoline, (substituted) pyridine and the like, and carboxymethyl heterocyclic alkali quaternary ammonium salt obtained by alpha-haloacetic acid, and then carrying out intermolecular addition polymerization reaction onquaternary ammonium salt of the heterocyclic alkali including the (substituted) quinoline, the (substituted) pyridine and the like. The acidification corrosion inhibitor disclosed by the invention has relatively good corrosion inhibition performance under the condition that common corrosion inhibition synergists including alkynol and the like do not need to be compounded; the use amount of the acidification corrosion inhibitor is less and the acidification corrosion inhibitor can reach, even be better than the requirements of an acidification corrosion inhibitor performance testing method andfirst-grade to third-grade standards in evaluation indexes SY/T 5405-1996 when being independently used.

Visible-Light-Induced Carbo-2-pyridylation of Electron-Deficient Alkenes with Pyridinium Salts

A simple and practical visible-light-induced carbo-2-pyridylation of electron-deficient alkenes with readily available N-benzoylmethylpyridinium bromides is reported. More than 40 examples are presented and proceed in greater than 80 % yield (on average)

One-pot synthesis of indolizine via 1,3-dipolar cycloaddition using a sub-equivalent amount of K2Cr2O7 as an efficient oxidant under base free conditions

A one-pot method for synthesizing multi-substituted indolizines from α-halo-carbonyl compounds, pyridines and electron deficient alkenes was developed. A sub-equivalent amount of potassium dichromate was used as an oxidant under base free conditions. The transformation developed should be of economic efficiency.

Novel indolizine derivatives with unprecedented inhibitory activity on human farnesyltransferase

The rational structural modification of new substituted indolizin-3-yl(phenyl)methanones 1a-i, 2a-i and 3a-i has greatly improved human farnesyltransferase inhibition. The para-bromophenyl analog 2f bearing an ester unit on the indolizine ring demonstrates the highest inhibition potential, with IC50 value of 1.3 ± 0.2 μM. The amidic series 1a-i proves to be the most promising for future modulations, particularly at the triple bond level.

Synthesis, photophysical, and electrochemical properties of 2,5-diaryl-indolizines

A variety of novel 2,5-diaryl-indolizines have been prepared through the palladium-catalyzed cross-coupling reactions of organozinc reagents prepared from 2-aryl-indolizines with aromatic halides. The photophysical properties of representative compounds indicate that the 2,5-diaryl-indolizines are promising candidates to be used in optoelectronic devices and biomolecular labeling. In addition, cyclic voltammetry studies of some nitrophenyl-substituted indolizines have shown evidences of an oxidation process without the correspondent reduction peak suggesting a dimerization reaction.

Copper acetate monohydrate: A cheap but efficient oxidant for synthesizing multi-substituted indolizines from pyridinium ylides and electron deficient alkenes

We report a highly practical one-pot method for synthesizing multi-substituted indolizines from ?±-halide carbonyl compounds, pyridines and electron deficient alkenes in the presence of copper acetate monohydrate and sodium acetate in DMF. A variety of function groups are tolerable in standard reaction conditions, including aldehyde. 36 examples were presented. The yield of indolizine was from moderate to high. Furthermore, multi-substituted indolizines can be prepared at gram scale by this method.

2- [ (2-SUBSTITUTED) -IND0LIZIN-3-YL] -2-OXO-ACETAMIDE DERIVATIVES AS ANTIFUNGAL AGENTS

The invention provides compounds of formula (I), and pharmaceutically acceptable salts thereof wherein: Rl, R2, R3, R4, R5, R6, R7, X and X1 are as defined herein. These compounds are useful in the manufacture of medicaments for use in the prevention or treatment of a fungal disease. Compounds of formula (I), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.

ANTIFUNGAL AGENTS

Compounds of formula (I), and pharmaceutically acceptable salts thereof, may be used in therapy, for example as antifungal agents: (I) wherein: Rl, R2, R3, R4, R5, R6, R7, X and X1 are as defined herein. Certain compounds of formula (I) are also provided. Compounds of formula (T), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.