69595-03-5Relevant academic research and scientific papers
Catalytic Acceptorless Dehydrogenation of Amino Alcohols and 2-Hydroxybenzyl Alcohols for Annulation Reaction under Neutral Conditions
Pandey, Akanksha M.,Digrawal, Naveen Kumar,Mohanta, Nirmala,Jamdade, Akash Bandu,Chaudhari, Moreshwar B.,Bisht, Girish Singh,Gnanaprakasam, Boopathy
, p. 8805 - 8828 (2021/07/20)
A base-free and acceptorless Ru-catalyzed dehydrogenative approach has been developed for the synthesis ofN-heterocycles by using 1,3-dicarbonyls and amino alcohols through a domino sequential enamine formation and intramolecular oxidative cyclization strategy. This unified approach is also applicable for the synthesis of O-heterocycles involving 2-hydroxybenzyl alcohol as a coupling reactant via consecutive C-alkylation and intramolecular cyclization steps. The present protocol is general for the synthesis of varieties of biologically important scaffolds, such as tetrahydro-4H-indol-4-one, 3,4-dihydroacridin-1(2H)-one, and tetrahydro-1H-xanthen-1-ones derivatives using a single catalytic system, viz. RuH2CO(PPh3)3. Environmentally benign H2O and H2are the only byproducts in this domino process. Moreover, RuH2CO(PPh3)3-catalyzed C3-alkylation of tetrahydro-4H-indol-4-one using alcohol as a alkylating partner is also described in this report. For the first time, a solvent-free gram-scale reaction for the acceptorless dehydrogenative annulation has been demonstrated. A plausible mechanism for the Ru-catalyzed base-free and acceptorless dehydrogenative annulation of amino alcohols or 2-hydroxybenzyl alcohols has been provided with several experimental investigations and spectroscopic evidence.
Tetrahydroindoles as Multipurpose Screening Compounds and Novel Sirtuin Inhibitors
Vojacek, Steffen,Schulig, Lukas,W?ssner, Nathalie,Geist, Norman,Langel, Walter,Jung, Manfred,Schade, Dennis,Link, Andreas
, (2019/03/26)
Indoles are privileged structures in medicinal and bioorganic chemistry that are particularly well suited to serve as platforms for diversity. Among many other therapeutic areas, the indole scaffold has been used to design aromatic compounds useful to interfere with enzymes engaged in the regulation of substrate acylation status, such as sirtuins. However, the planarity of the indole ring is not necessarily optimal for all target enzymes, especially when functionalization with aromatic side chains is required. Replacement of flat scaffolds by nonplanar molecular cores dominated by sp3 hybridization is a common strategy to avoid the disadvantages associated with poor solubility and high promiscuity, while covering less-well-explored areas of chemical space. Thus, we synthesized fragment-like tetrahydroindoles suitable for fragment-based drug discovery as well as a well-characterized small library intended as multipurpose screening compounds. For proof of principle, these compounds were screened against sirtuins 1–3, enzymes known to be addressable by indoles. We found that 2,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamides are potent and selective SIRT2 inhibitors. Compound 16 t displayed an IC50 value of 0.98 μm and could serve as exquisite starting point for hit-to-lead profiling.
OMEGA-AMINO ACID DERIVATIVES OF BENZENE, PYRIDINE, AND PYRIDAZINE COMPOUNDS
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Paragraph 0269; 0270, (2015/12/23)
Disclosed are compounds and pharmaceutically acceptable salts of Formula I wherein R1, R2, R3, R4, R5, R6, R7, n, Q1, Q2, Q3, Y, and X1/sub
De novo design of non-coordinating indolones as potential inhibitors for lanosterol 14-α-demethylase (CYP51)
Gonzalez-Chavez, Rodolfo,Martinez, Roberto,Torre-Bouscoulet, Maria Eugenia,Gallo, Marco,Gonzalez-Chavez, Marco Martin
, p. 16 - 24 (2014/01/23)
The development of antifungal drugs that inhibit lanosterol 14-α-demethylase (CYP51) via non-covalent ligand interactions is a strategy that is gaining importance. A series of novel tetraindol-4-one derivatives with 1- and 2-(2,4-substituted phenyl) side chains were designed and synthesized based on the structure of CYP51 and fluconazole. The antifungal activities of these derivatives against eight human pathogenic filamentous fungi and yeast strains were evaluated in vitro by measuring the minimal inhibitory concentrations. Nearly all tested compounds 8a-g displayed activity against Candida tropicalis, Candida guilliermondii and Candida parapsilosis with a minimum inhibitory concentration (MIC) value until 8 μg mL-1, on the other hand compounds 7a-g showed activity against Aspergillus fumigatus with a MIC value of 31.25 μg mL-1. A molecular modeling study of the binding interactions between compounds 6, 7d, 8g and the active site of MtCYP51 was conducted based on the computational docking results.
HYDROXAMATE DERIVATIVES FOR HDAC INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THEREOF
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Paragraph 0759-0761, (2014/10/29)
The present invention relates to a novel hydroxamate derivatives, more specifically, to novel hydroxamate derivatives having inhibitory activity against Histone Deacetylase (HDAC), isomers thereof, pharmaceutically acceptable salts thereof, hydrates or solvates thereof, use for preparing pharmaceutical compositions, pharmaceutical compositions comprising the same, treatment method using said composition, and a preparing method of novel hydroxamate derivatives. The novel selective hydroxamate derivatives having inhibitory activity against Histone Deacetylase (HDAC) compositions can be used for treatment of inflammatory disease, rheumatoid arthritis, or degenerative disease.
HYDROXAMATE DERIVATIVES FOR HDAC INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THEREOF
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Page/Page column 163; 164, (2013/05/21)
The present invention relates to a novel hydroxamate derivatives, more specifically, to novel hydroxamate derivatives having inhibitory activity against Histone Deacetylase (HDAC), isomers thereof, pharmaceutically acceptable salts thereof, hydrates or solvates thereof, use for preparing pharmaceutical compositions, pharmaceutical compositions comprising the same, treatment method using said composition, and a preparing method of novel hydroxamate derivatives. The novel selective hydroxamate derivatives having inhibitory activity against Histone Deacetylase (HDAC) compositions can be used for treatment of inflammatory disease, rheumatoid arthritis, or degenerative disease.
TETRAHYDROINDOLONE AND TETRAHYDROINDAZOLONE DERIVATIVES
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Page/Page column 125-126, (2008/06/13)
Disclosed are compounds and pharmaceutically acceptable salts of Formula (I): wherein R1, R2, R3, R4, R5, R6, R7, n, Q1, Q2, Q3, Y, and X1-X4 are as defined
NEW C-N-C BOND FORMATION REACTION USING NITROGENATION-TRANSMETALLATION PROCESS. NOVEL RING CONSTRUCTION OF INDOLE AND QUINOLINE DERIVATIVES.
Mori, Miwako,Uozumi, Yasuhiro,Shibasaki, Masakatsu
, p. 819 - 830 (2007/10/02)
Ketones and aryl or vinyl halides couple to give divinyl- or arylvinylamines in the presence of the titaniumisocyanate complex (1) and a palladium catalyst, via transmetallation of the titano imine complex (3) with aryl- or vinylpalladium bromide.
New C-N-C Bond Formation Reaction using the Nitrogenation-transmetallation Process
Uozumi, Yasuhiro,Mori, Miwako,Shibasaki, Masakatau
, p. 81 - 83 (2007/10/02)
Ketones and aryl or vinyl halides couple to give divinyl or arylvinyl amines in the presence of the titanium isocyanate complex 1 and a palladium catalyst, via transmetallation of the titano imine complex 6 with aryl or vinyl palladium bromide (THF tetrahydrofuran).
