82789-40-0Relevant articles and documents
β-Carboline tethered cinnamoyl 2-aminobenzamides as class I selective HDAC inhibitors: Design, synthesis, biological activities and modelling studies
Godugu, Chandraiah,Kamal, ahmed,Lakshmi Manasa, Kesari,Namballa, Hari Krishna,Shankaraiah, Nagula,Soni, Jay Prakash,anchi, Pratibha
, (2021/11/11)
The effect of β-carboline motif as cap for HDAC inhibitors containing cinnamic acid as linker and benzamides as zinc binding group was examined in this study. A series of β-carboline-cinnamide conjugates have been synthesized and evaluated for their HDAC inhibitory activity and in vitro cytotoxicity against different human cancer cell lines. Almost all the compounds exhibited superior HDAC inhibitory activity than the standard drug Entinostat for in vitro enzymatic assay. Among the tested compounds, 7h displayed a noteworthy potency with an IC50 value of 0.70 ± 0.15 μM against HCT-15 cell line when compared to the standard drug Entinostat (IC50 of 3.87 ± 0.62 μM). The traditional apoptosis assays such as nuclear morphological alterations, AO/EB, DAPI, and Annexin-V/PI staining revealed the antiproliferative activity of 7h while depolarization of mitochondrial membrane potential by JC-1 was observed in dose-dependent manner. Cell cycle analysis also unveiled the typical accumulation of cells in G2M phase and sub-G1/S phase arrest. In addition, immunoblot analysis for compound 7h on HCT-15 indicated selective inhibition of the protein expression of class I HDAC 2 and 3 isoforms. Molecular docking analysis of compound 7h revealed that it can prominent binding with the active pocket of the HDAC 2. These finding suggest that the compound 7h can be a promising lead candidate for further investigation in the development of novel anti-cancer drug potentially inhibiting HDACs.
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.
Simple and efficient method for aromatization of tetrahydro-β-carbolines by using K2S2O8 as a catalyst and its antimicrobial activity comparison with molecular docking studies
Kurumanna,Ashok,Rambabu,Sonyanaik,Ravi,Madhu,Sakram
, p. 2703 - 2711 (2017/12/26)
A novel and efficient aromatization of tetrahydro-β-carbolines under mild conditions using K2S2O8 as a catalyst was developed. The method is applicable for all kinds of C1 substituted systems. All synthesized compounds were screened for their in vitro antibacterial activity against Staphylococus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumonia, as well as fungi, such as Aspergillus flavus and Fusarium oxysporum. Compounds 4b, 4g, 4i, and 4k demonstrated excellent in vitro antibacterial and antifungal activities than the standard drugs. The docking studies were carried out for most active compounds 4b, 4g, 4i, and 4k.
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.
Chemical compounds
-
, (2008/06/13)
Compounds of the general structural formula and use of the compounds and salts and solvates thereof, as therapeutic agents.
Potent 1,3-disubstituted-9H-pyrido[3,4-b]indoles as new lead compounds in antifilarial chemotherapy
Srivastava, Sanjay K.,Agarwal, Alka,Chauhan, Prem M. S.,Agarwal, Shiv K.,Bhaduri, Amiya P.,Singh, Som N.,Fatima, Nigar,Chatterjee, Ranjit K.
, p. 1667 - 1672 (2007/10/03)
Substituted 9H-pyrido[3,4-b]indoles (β-carbolines), identified in our laboratory as potential pharmacophores for designing macrofilaricidal agents, have been explored further for identifying the pharmacophore responsible for the high order of adulticidal
Method and compositions using 1-aryl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid for treating depression
-
, (2008/06/13)
Treatment of central nervous system depression in a mammal using method and compositions employing 1-aryl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acids, esters and pharmaceutically-acceptable salts.
