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A method for the room temperature deoxyfluorination of benzaldehydes and alpha-ketoesters using sulfuryl fluoride and Me4NF is described. A large scope of aryl and heteroaryl substrates is demonstrated, and this method compares favorably to other common deoxyfluorination methods for many substrates.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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A method for the room temperature deoxyfluorination of benzaldehydes and alpha-ketoesters using sulfuryl fluoride and Me4NF is described. A large scope of aryl and heteroaryl substrates is demonstrated, and this method compares favorably to other common deoxyfluorination methods for many substrates.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H966N – PubChem

 

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Azastilbenes. 1. Synthesis, Characterization, and Structure

The synthesis of several symmetric and asymmetric azastilbenes is described, and their spectral characteristics (NMR, mass, UV, IR) are given.Four of them are new compounds, namely, 1,2-di(4-isoquinolyl)ethylene, 1-(3-pyridyl)-2-(2-pyrazinyl)ethylene, 1-(3-pyridyl)-2-(4-isoquinolyl)ethylene, and 1-(2-pyrazinyl)-2-(4-isoquinolyl)ethylene.The molecular structure and crystalline stacking of some of these azastilbenes and of the quaternary salts of 1,2-di(2-pyridyl)ethylene and 1,2-di(4-pyridyl)ethylene have been determined by X-ray diffraction on a single crystal and their characteristic parameters indicated.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H975N – PubChem

 

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Aromatic hydroxamic acid compounds, their production and use

The present invention relates to a compound of the formula: STR1 wherein Ar represents an optionally substituted aromatic group; Q represents a divalent aliphatic hydrocarbon group; R1 represents hydrogen, cyano, an optionally substituted hydrocarbon group, a group of the formula: STR2 wherein R3 and R4 independently represent hydrogen, acyl or an optionally substituted hydrocarbon group, or R3 and R4 jointly form a ring, or acyl; R2 represents acyl; ……… represents a single bond or a double bond; m represents 1 or 2 or a salt, a process of producing thereof and an anti-neurodegenerative composition.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H937N – PubChem

 

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ISOQUINOLINESULFONYL DERIVATIVE AS RHO KINASE INHIBITOR

The present invention discloses a class of isoquinolinesulfonyl derivatives as RHO kinase inhibitors, and pharmaceutical compositions thereof, and relates to pharmaceutically acceptable uses thereof. Specifically, the present invention relates to a compound as represented by formula (I), or a pharmaceutically acceptable salt thereof.

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Isoquinoline – Wikipedia,
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Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5 muM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H972N – PubChem

 

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A new class of simple synthetic antimitotic compounds based on 2-aroylindoles was discovered. (5-Methoxy-1H-2-indolyl)-phenylmethanone (1) as well as analogous 3-fluorophenyl- (36) and 3-methoxyphenyl (3) derivatives displayed high cytotoxicity of IC50 = 20 to 75 nM against the human HeLa/KB cervical, SK-OV-3 ovarian, and U373 astrocytoma carcinoma cell lines. The inhibition of proliferation correlated with the arrest in the G2/M phase of the cell cycle. In in vitro assays with tubulin isolated from bovine brain, in general antiproliferative activity correlated with inhibition of tubulin polymerization. Thus, the antimitotic activity of 2-aroylindoles is explained by interference with the mitotic spindle apparatus and destabilization of microtubules. In contrast to colchicine, vincristine, nocodazole, or taxol, 1 did not significantly affect the GTPase activity of beta-tubulin. Interestingly, selected compounds inhibited angiogenesis in the chorioallantoic membrane (CAM) assay. In xenograft experiments, 1 was highly active after oral administration at 200 mg/kg against the human amelanocytic melanoma MEXF 989 in athymic nude mice. We conclude, that 2-aroylindoles constitute an interesting new class of antitubulin agents with the potential to be clinically developed for cancer treatment.

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Isoquinoline – Wikipedia,
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Copper-catalyzed retro-aldol reaction of beta-hydroxy ketones or nitriles with aldehydes: Chemo- and stereoselective access to (E)-enones and (E)-acrylonitriles

A copper-catalyzed transfer aldol type reaction of beta-hydroxy ketones or nitriles with aldehydes is reported, which enables chemo- and stereoselective access to (E)-alpha,beta-unsaturated ketones and (E)-acrylonitriles. A key step of the in situ copper(i)-promoted retro-aldol reaction of beta-hydroxy ketones or nitriles is proposed to generate a reactive Cu(i) enolate or cyanomethyl intermediate, which undergoes ensuing aldol condensation with aldehydes to deliver the products. This reaction uses 1.2 mol% Cu(IPr)Cl (IPr denotes 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) as the catalyst in the presence of 6.0 mol% NaOtBu cocatalyst at room temperature or 70 C. A range of aryl and heteroaryl aldehydes as well as acrylaldehydes are compatible with many useful functional groups being tolerated. Under the mild and weakly basic conditions, competitive Cannizzaro-type reaction of benzaldehydes and side reactions of base-sensitive functional groups can be effectively suppressed, which show synthetic advantages of this reaction compared to classic aldol reactions. The synthetic potential of this reaction is further demonstrated by the one-step synthesis of biologically active quinolines and 1,8-naphthyridine in excellent yields (up to 91%). Finally, a full catalytic cycle for this reaction has been constructed using DFT computational studies in the context of a retro-aldol/aldol two-stage mechanism. A rather flat reaction energy profile is found indicating that both stages are kinetically facile, which is consistent with the mild reaction conditions.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H982N – PubChem

 

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FARNESYL PROTEIN TRANSFERASE INHIBITORS

Disclosed are compounds of the formula: wherein R8 represents a cyclic moiety to which is bound an imodazolylalkyl group; R9 represents a carbamate, urea, amide or sulfonamide group; and the remaining substituents are as defined herein. Also disclosed is a method of treating cancer and a method of inhibiting farnesyl protein transferase using the disclosed compounds

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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New strategy for the preparation of nitrogen- and phosphorus-containing chiral polyfunctional secondary alcohols

The use of borane-derived protecting groups for aldehydes containing pyridine and phosphine functionalities allows the performance of highly enantioselective additions of functionalized diorganozincs leading to polyfunctional chiral hydroxy-pyridines and -phosphines with excellent enantioselectivity.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem