Category: isoquinoline

Hosseinzadeh, Leila published the artcileSynthesis of 4-phenyl-4,5-dihydropyranopyrazolone derivatives with activated potassium carbonate: evaluation of anticancer activity on cancer cell lines and apoptosis mechanism, Related Products of isoquinoline, the main research area is phenyl dihydropyranopyrazolone derivative potassium carbonate apoptosis anticancer activity.

A green and efficient one-pot, four-component synthesis of 4-phenyl-4,5-dihydropyranopyrazolone derivatives 5a-5l is described in ethanol-water with activated potassium carbonate and evaluation of anticancer activity on cancer cell lines and apoptosis mechanism is also investigated. This method provides several advantages such as environmental friendliness, shorter reaction time, excellent yields, and simple workup procedure. The in vitro cytotoxic activity of the synthesized compounds was investigated against cancer cell lines (PC-3, MCF-7, and A-2780) in comparison with doxorubicin, a well-known anticancer drug, using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide colorimetric assay. Also apoptosis studies were investigated by caspase-3 and caspase-9 enzymes and mitochondrial membrane potential. Our compounds showed acceptable and moderate cytotoxicity compared with doxorubicin in the studied cell lines. The compounds 5g in PC3 cell line (half maximal inhibitory concentration (IC50 = 104 μM)), 5g and 5i in MCF7 cell line (IC50 = 23 and 87 μM, resp.), and 5g-5i in A2780 cell line (IC50 = 60, 50, and 31 μM, resp.) showed the best results close to the control drug doxorubicin. The compound 5h showed significant result in the activation of caspase-3 and caspase-9 enzymes in comparison with the control. Only the 5g in MCF7 cells and the 5g-5i derivatives in A2780 cells caused increased mitochondrial membrane potential compared to the control group.

Journal of Reports in Pharmaceutical Sciences published new progress about Antitumor agents. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Xu, Geng published the artcileMitochondria-Targeted Triphenylphosphonium Conjugated C-3 Modified Betulin: Synthesis, Antitumor Properties and Mechanism of Action, Product Details of C9H10O3, the main research area is triphenylphosphonium conjugated betulin apoptosis cell cycle arrest antitumor; antiproliferation; betulin; conjugation; drug discovery; mitochondria; structure-activity relationship; triphenylphosphonium.

A series of mitochondria-targeted triphenylphosphonium conjugated C-3 modified betulin were synthesized and evaluated against tumor cells. As a result, a new derivative 13 i, the conjugate of 3-O-(3′-acetylphenylacetate)-betulin with triphenylphosphonium, was identified as the one with the best anti-tumor effect. Conjugate 13 i significantly inhibited HCT116 cells with IC50 at 0.66 μM. While betulin, C-3 modified betulin, and the triphenylphosphonium moiety showed no inhibition of HCT116 cell proliferation at 20 μM. More importantly, 13 i exhibited a more cytotoxic effect against the tumor cell HCT116 than normal cell NCM460. Mode of action studies demonstrated that 13 i induced the G2/M phase cell cycle arrest and apoptosis in HCT116 cells through the mitochondrial pathway. Structure-activity relationship anal. revealed that integration of triphenylphosphonium moiety into the C-28 of betulin can greatly improve cytotoxicity. Appropriate modification on C-3 of the conjugate would improve the selectivity.

ChemMedChem published new progress about Antitumor agents. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Product Details of C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Pereira, Daniela published the artcileDesign and synthesis of new inhibitors of p53-MDM2 interaction with a chalcone scaffold, Related Products of isoquinoline, the main research area is chalcone derivative anticancer agent p53 MDM2 interaction docking cancer.

The virtual screening of a library of chalcone derivatives led us to the identification of potential new MDM2 ligands. The chalcones with the best docking scores obeying the Lipinski rule of five were subsequently prepared by base-catalyzed aldol reactions. The activity of these compounds as inhibitors of p53-MDM2 interaction was investigated using a yeast-based screening assay. Using this approach two chalcones (3 and 4) were identified as putative small mol. inhibitors of p53-MDM2 interaction. The activity of both chalcones was further investigated in a panel of human tumor cells. Chalcones 3 and 4 revealed a pronounced tumor cell growth inhibitory effect on tumor cell lines. Addnl., chalcone 4 caused alterations in the cell cycle profile, induced apoptosis and increased the levels of p53, p21 and PUMA proteins in NCI-H460 cells. Computational docking studies allowed to predict that, like nutlin-3A (a well-known small-mol. inhibitor of p53-MDM2 interaction), chalcones 3 and 4 bind to the p53-binding site of MDM2. The results here presented will be valuable for the structure-based design of novel and potent p53-MDM2 inhibitors.

Arabian Journal of Chemistry published new progress about Antitumor agents. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Guan, Hong-Hsiang published the artcilePlumbagin, a Natural Product with Potent Anticancer Activities, Binds to and Inhibits Dihydroorotase, a Key Enzyme in Pyrimidine Biosynthesis, Name: 3,5-Diamino-1,2,4-triazole, the main research area is plumbagin anticancer agent dihydroorotase breast cancer; 4T1 cell; CAD; allantoinase; anticancer; crystal structure; dihydroorotase; dihydropyrimidinase; drug design; plumbagin; pyrimidine biosynthesis.

Dihydroorotase (DHOase) is the third enzyme in the de novo biosynthesis pathway for pyrimidine nucleotides, and an attractive target for potential anticancer chemotherapy. By screening plant extracts and performing GC-MS anal., we identified and characterized that the potent anticancer drug plumbagin (PLU), isolated from the carnivorous plant Nepenthes miranda, was a competitive inhibitor of DHOase. We also solved the complexed crystal structure of yeast DHOase with PLU (PDB entry 7CA1), to determine the binding interactions and investigate the binding modes. Mutational and structural analyses indicated the binding of PLU to DHOase through loop-in mode, and this dynamic loop may serve as a drug target. PLU exhibited cytotoxicity on the survival, migration, and proliferation of 4T1 cells and induced apoptosis. These results provide structural insights that may facilitate the development of new inhibitors targeting DHOase, for further clin. anticancer chemotherapies.

International Journal of Molecular Sciences published new progress about Antitumor agents. 1455-77-2 belongs to class isoquinoline, name is 3,5-Diamino-1,2,4-triazole, and the molecular formula is C2H5N5, Name: 3,5-Diamino-1,2,4-triazole.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Al Otaibi, Ahmed published the artcileA methanol and protic ionic liquid Ugi multicomponent reaction path to cytotoxic α-phenylacetamido amides, Computed Properties of 86-51-1, the main research area is protic ionic liquid alpha phenylacetamido amides anticancer.

The Ugi four component reaction of an aldehyde, amine, isocyanide and an ethanoic acid was effected smoothly in protic ionic liquids ethylammonium nitrate (EAN) and propylammonium nitrate (PAN) to afford analogs of α-phenylacetamido amides in good to excellent isolated yields. The corresponding reactions in [BMIM][PF6] and the protic ionic liquid ethanolammonium nitrate (ETAN) failed. Microwave irradiation in EAN facilitated rapid access to three focused libraries, based on the parent isocyanide: cyclohexyl isocyanide, benzyl isocyanide and Et isocyanoacetate. Anal. of the structure activity relationship data suggested the presence of a bulky moiety originating from the isocyanide (cyclohexyl and benzyl) enhanced cytotoxicity. Removal of the acetylenic H-atom from the ethanoic acid moiety was detrimental to cytotoxicity. The most active analogs produced, N-(2-cyclohexylamino)-1-(4-methoxyphenyl)-2-oxoethyl-N-(3,5-dimethoxyphenyl)propiolamide, returned average GI50 values of ≤1 μM across the cancer cell lines evaluated. Combined, these data suggest that analogs of this nature are interesting potential anti-cancer development leads.

RSC Advances published new progress about Antitumor agents. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Computed Properties of 86-51-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

El-Kalyoubi, Samar A. published the artcileUracil as a Zn-Binding Bioisostere of the Allergic Benzenesulfonamide in the Design of Quinoline-Uracil Hybrids as Anticancer Carbonic Anhydrase Inhibitors, Application of 1-Methylurea, the main research area is aminothioxo pyrimidinyliminomethyl quinolinone preparation carbonic anhydrase inhibition antitumor SAR; anticancer; carbonic anhydrase; quinoline; uracil; zinc-binding group.

A series of quinoline-uracil hybrids has been rationalized and synthesized. The inhibitory activity against hCA isoforms I, II, IX, and XII was explored. Compoundsmonstrated powerful inhibitory activity against all tested hCA isoforms. Compound (E)-6-Amino-5-(((6-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)methylene)amino) pyrimidine-2,4(1H,3H)-dione displayed the best selectivity profile with good activity. Compound (E)-6-Amino-1-methyl-5-(((2-oxo-1,2-dihydroquinolin-3-yl)methylene)amino) pyrimidine-2,4(1H,3H)-dione displayed the best activity profile with minimal selectivity. Compound (E)-3-(((6-Amino-1-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidin-5yl)imino)methyl)-6-methoxyquinolin-2(1H)-one emerged as the best congener considering both activity (IC50 = 140 and 190 nM for hCA IX and hCA XII, resp.) and selectivity (S.I. = 13.20 and 9.75 for II/IX, and II/XII, resp.). The most active hybrids were assayed for antiproliferative and pro-apoptotic activities against MCF-7 and A549. In silico studies, mol. docking, physicochem. parameters, and ADMET anal. were performed to explain the acquired CA inhibitory action of all hybrids. A study of the structure-activity relationship revealed that bulky substituents at uracil N-1 were unfavored for activity while substituted quinoline and thiouracil were effective for selectivity.

Pharmaceuticals published new progress about Antitumor agents. 598-50-5 belongs to class isoquinoline, name is 1-Methylurea, and the molecular formula is C2H6N2O, Application of 1-Methylurea.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Gorle, Sridevi published the artcileSynthesis and anticancer activity of novel pyrazolo[4′,3′:5,6]pyrano[2,3-d] pyrimidin-5(2H)-one derivatives, Formula: C9H10O3, the main research area is pyrazolopyranopyrimidinone preparation antitumor SAR.

A novel sequence of pyrazole connected pyrano[2,3-d]-pyrimidin-5(2H)-ones, compounds I [R = 4-Me, 2-Cl, 2-Br, etc.] were designed, prepared and screened for their cytotoxicity against four human cancer cell lines like MCF-7 (breast), HeLa (cervical), CaCo2 (colorectal) and HepG2 (liver) by MTT assay. Most of the tested mols. were exhibited good to excellent cytotoxicity against all tested cell lines when compared to the standard drug Doxorubicin. Amongst all the synthesized target compounds, the mols. compounds I [R = 2,3,4-triMeO, 3,4,5-triMeO] exhibited the excellent anticancer activity against all the human MCF-7, HeLa, CaCo2 and HepG2 tumor cell lines, with the inhibitory concentration (IC50) values of 14, 14, 13, & 16μg mL-1 and 16, 14, 15 & 17μg mL-1, resp., while, compounds I [R = 2,3-diMeO, 3,4-diMeO] revealed good inhibitory activity against all screened cell lines with the IC50 values of 22, 25, 25 & 24μg mL-1 and 21, 20, 21, & 20μg mL-1. All the novel target mols. were determined and characterized by various spectroscopic (1H NMR, 13C NMR and HR-MS) anal.

Chemical Data Collections published new progress about Antitumor agents. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Formula: C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zhang, Yan published the artcileFourfold-Interpenetrated MOF [Ni(pybz)2] as Coating Material in Gas Chromatographic Capillary Column for Separation, Related Products of isoquinoline, the main research area is nickel pyridylbenzoato complex preparation crystal structure gas adsorption DFT; alc aldehyde ketone carboxylic acid ethers ester amine separation.

A 4-fold interpenetrated diamond-like topol. metal-organic framework (MOF), Ni(pybz)2 [pybz = 4-(4-pyridyl)benzoate] was successfully synthesized and fully characterized. This MOF can serve as coating material in gas chromatog. capillary column for the separation of some low b.p. essential oils. The prepared columns have good recognition ability and excellent selectivity toward organic compounds, including alcs., aldehydes, ketones, carboxylic acid, ethers, ester, and amines. The strained metal sites, van der Waals interactions, C-H···π attraction, and weak nonclassical hydrogen bond contribute to the recognition and selectivity of prepared columns. The grand canonical Monte Carlo technique was used to simulate the interactions of the adsorbates with MOF. The calculated van der Waals energies agree with the results of gas chromatog. separation

Inorganic Chemistry published new progress about Coating materials. 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Wu, Wen-Biao published the artcileMe2(CH2 = CH)SiCN: a bifunctional ethylene equivalent for Diels-Alder reaction based controllable tandem synthesis, HPLC of Formula: 21834-92-4, the main research area is cyclohexenyl ketone perpn crystal structure mol; cyclohexancarbonitrile derivative perpn crystal structure mol; ylide aldehyde tandem reaction bifunctional silyl reagent.

A bifunctional silyl reagent Me2(CH2=CH)SiCN was developed as a novel ethylene equivalent for the Diels-Alder (DA) reaction. The use of this reagent enabled the controllable synthesis of value-added cyclohexenyl ketones I [R = Ph, 4-MeC6H4, 3-FC6H4, etc.; R1 = Me, Et, Ph, etc.], II [R2 = H, 7-OMe, 6-Br; X = CH2, O] or 2-acyl cyclohexancarbonitrile derivatives III [R3 = Me, cyclopropyl, iPr, Ph; R4 = Ph, 4-MeC6H4, 4-FC6H4, etc.] through a five- or six-step tandem sequence based on a Wittig/cyanosilylation/DA reaction/retro-cyanosilylation/isomerization of P-ylides and enals that involved a temporary silicon-tethered intramol. DA reaction.

Chemical Science published new progress about Crystal structure. 21834-92-4 belongs to class isoquinoline, name is 5-Methyl-2-phenylhex-2-enal, and the molecular formula is C13H16O, HPLC of Formula: 21834-92-4.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Vavaiya, Bhavinkumar published the artcileIn silico and in vitro antitubercular studies for nitrogen rich hybrids of homopiperazine-pyrimidine-pyrazole adducts, Category: isoquinoline, the main research area is Mycobacterium antitubercular nitrogen rich hybrid homopiperazine pyrimidine pyrazole.

Novel homopiperazine-pyrimidine-pyrazole hybrids (3a-j) were synthesized using Et 2-cyanoacetate and 4,6-dichloropyrimidine as starting materials by a multi-step process to afford Et 5-amino-1-(6-chloropyrimidin-4-yl)-1H-pyrazole-4-carboxylate in good yields using polar protic media. The intermediate 1, in two steps, chloroamine condensation followed by acid amine coupling, furnished the title compounds Et 5-amino-1-(6-(4-substituted aryl-1,4-diazepan-1-yl)pyrimidin-4-yl)-1H-pyrazole-4-carboxylate (3a-j). The synthesized compounds were docked in the crystal structure of Mycobacterium tuberculosis (PDB ID: 4TRO) to get insights into structural requirements for antitubercular activity. In vitro antitubercular activity against M. tuberculosis H37Rv strains showed that compounds 3a, 3d, 3e and 3g were found to be the most potent (Docking score: > -21; MIC = 1.6 μg/mL) among the synthesized mols. All the synthesized compounds showed acceptable drug-like properties which make them suitable for further lead modification using in silico design approaches.

Asian Journal of Chemistry published new progress about Crystal structure. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem