82789-21-7Relevant academic research and scientific papers
Synthesis, Antileishmanial Activity and Spin Labeling EPR Studies of Novel β-Carboline-Oxazoline and β-Carboline-Dihydrooxazine Derivatives
Alonso, Antonio,Alonso, Laís,Baréa, Paula,Nakamura, Celso V.,Sarragiotto, Maria H.,da Costa, Willian F.,de Oliveira, Aline R.,de Paula, Jéssica C.
, p. 1170 - 1185 (2020/10/14)
A series of novel 1-(substituted-phenyl)-3-(4,5-dihydro-1,3-oxazol-2-yl)-9H-β-carboline (8a-8i) and 1-(substituted-phenyl)-3-(5,6-dihydro-4H-1,3-oxazin-2-yl)-9H-β-carboline (9a-9h) derivatives, as well as their respective N-(chloroalkyl)-1-(substituted-phenyl)-9H-β-carboline-3-carboxamide precursors (6a-6i and 7a-7h), were synthesized and evaluated for their in vitro antileishmanial activity against promastigote and intracellular amastigote forms of Leishmania amazonensis. Compounds 8d, 8i, 9e and 9h exhibited significant activity for both promastigote and amastigote forms, with IC50 (50% inhibitory concentration) values ranging from 2.9 to 23.0 μM. In addition, spin label electron paramagnetic resonance (EPR) spectroscopy studies were carried out for the most active compounds against L. amazonensis promastigotes. The studies indicated that the tested compounds cause strong stiffness in the parasite plasma membrane and are capable of inducing internal metalloproteins oxidation of the parasite, resulting in their cross-linking to skeletal proteins. Compounds 8d and 8i produced the largest effect, showing that the presence of oxazoline group at C-3 of β-carboline nucleus is important for antileishmanial activity.
β-Carboline and N-hydroxycinnamamide hybrids as anticancer agents for drug-resistant hepatocellular carcinoma
Ling, Yong,Gao, Wei-Jie,Ling, Changchun,Liu, Ji,Meng, Chi,Qian, Jianqiang,Liu, Siqun,Gan, Huiling,Wu, Hongmei,Tao, Jinhua,Dai, Hong,Zhang, Yanan
, p. 515 - 526 (2019/03/08)
In an effort to develop anticancer agents that may overcome drug resistance, the number one reason in caner death, we have developed a series of novel hybrids of β-carboline and N-hydroxycinnamamide as histone deacetylase (HDAC) inhibitors. Most of the hybrids 13a-p showed strong antiproliferative effects with low-micromolar IC50 values against four human cancer cells. The most potent compound of series 13p exhibited high HDAC1/6 inhibitory effects, and also increased the acetylation levels of histone H3, H4 and α-tubulin. Importantly, 13p demonstrated high anticancer potency against drug-sensitive HepG2 and Bel7402 cells and drug-resistant Bel7402/5FU cells. Hybrid 13p triggered significant apoptosis by regulating apoptotic relative proteins expression in these Bel7402/5FU cells. Finally, 13p induced a substantial amount of autophagic flux activity by the accretion of the expression of LC3-II and the degeneration of expression of p62 and LC3-I in Bel7402/5FU cells. Overall, 13p is a novel β-carboline/N-hydroxycinnamamide hybrid with significant anticancer potency that warrants further evaluation for the treatment of drug-resistant hepatocellular carcinoma.
Dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acids and their esters with dimethyl sulfoxide
Abramyants,Lomov,Zavyazkina
, p. 1610 - 1615 (2017/01/28)
Oxidative dehydrogenation of 1-aryl(hetaryl)-1,2,3,4-tetrahydro-9Н-β-carboline-3-carboxylic acids derivatives with dimethyl sulfoxide leads to the formation of 1-aryl(hetaryl)-9Н-β-carbolines. Simultaneously with the dehydrogenation decarboxylation occurs
Convenient synthesis of 1-aryl-9H-β-carboline-3-carbaldehydes and their transformation into dihydropyrimidinone derivatives by Biginelli reaction
ábrányi-Balogh, Péter,Dancsó, András,Frigyes, Dávid,Volk, Balázs,Keglevich, Gy?rgy,Milen, Mátyás
, p. 5711 - 5719 (2015/03/30)
In the present work, a practical synthesis of 1-aryl-β-carboline-3-carbaldehydes as versatile building blocks and their application in Biginelli reaction is reported. The starting material of the four-step synthesis is racemic tryptophan methyl ester. The procedure involves a Pictet-Spengler cyclization, a dehydrogenation, an ester reduction, and an alcohol oxidation step. The β-carboline-3-carbaldehydes were further transformed using a Biginelli reaction into derivatives containing a pharmacologically significant dihydropyrimidine ring at position-3.
Highly efficient Lewis acid-catalysed Pictet-Spengler reactions discovered by parallel screening
Srinivasan, Natarajan,Ganesan
, p. 916 - 917 (2007/10/03)
High yielding Lewis acid-catalysed one-pot Pictet-Spengler reactions of tryptophan methyl ester and tryptamine with aliphatic and aromatic aldehydes were achieved in short reaction times with the aid of microwave irradiation.
Possible Anthelmintic Agents: Syntheses of 1,3-Disubstituted 1,2,3,4-Tetrahydro-9H-pyridoindoles and 6,8-Disubstituted 7,8,9,14b-Tetrahydro-14H-quinazolinopyridoindoles
Kumar, Shiv,Roy, Jalpana,Seth, M.,Bhaduri, A. P.
, p. 54 - 59 (2007/10/02)
Pictet-Spengler reaction of tryptophan methyl ester with aromatic and heterocyclic aldehydes gives 1-substituted 3-carbomethoxy-1,2,3,4-tetrahydro-9H-pyridoindoles (1 - 9).Ring closure of 1-(o-aminophenyl)-3-carbomethoxy-1,2,3,4-tetrahydro-9H-pyridoindole (26) or its hydrazide (28) with N-methoxycarbonyl-S-methylisothiourea gives 6,8-disubstituted 7,8,9,14b-tetrahydro-14H-quinazolinopyridoindoles (34 and 29, respectively).The former class of compounds exhibit activity (60 - 86percent) of worm clearance against A. ceylanicum in hamsters whilea member of the latter class of compounds (34) exhibits 100percent of activity only against H. nana at 250 mg/kg in mice.Other compounds which exhibit worm clearance of less than 50percent have not been reported here.
1H- and 13C-NMR Spectroscopic Assigment to the cis and trans Isomers of Some 1-Aryl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic Acids and their Methyl Esters
Pindur, Ulf
, p. 361 - 368 (2007/10/02)
The cis and trans isomers of the tetrahydro-β-carbolines 3 and 4 were assigned on the basis of the shifts of the NMR signals of the proton at C-1 and of the carbon atoms C-1 and C-3.
