- A new (3+3) annulation route to isoquinoline-3-carboxylates
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A new synthesis of isoquinoline-3-carboxylates based on the palladium(0)-catalysed Heck-type arylation of 2-amidoacrylates with the appropriate 2-substituted iodobenzene is reported.
- Chattopadhyay, Shital K,Maity, Susama,Pal, Benoy K,Panja, Srikanta
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- β-Carbolines: Synthesis and neurochemical and pharmacological actions on brain benzodiazepine receptors
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The authors have prepared a series of tetrahydro-β-carbolines (THβC), β-carbolines (β-C), and other nitrogen heterocycles and evaluated them in vitro with respect to their ability to bind to benzodiazepine receptors. The fully aromatic β-C's were more pot
- Cain,Weber,Guzman,Cook,Barker,Rice,Crawley,Paul,Skolnick
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- Palladium-catalysed cascades triggered by dehydrogenation of secondary or tertiary amines: Access to bridged- and fused-ring heterocycles
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Palladium-catalysed cascades triggered by dehydrogenation of secondary or tertiary amines and trapping the intermediate imines with cycloadditions and Mannich reactions result in a range of bridged- and fused-ring heterocyclic motifs in moderate to good y
- Grigg, Ronald,Somasunderam, Anoma,Sridharan, Visuvanathar,Keep, Ann
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- Synthesis and assay of isoquinoline derivatives as HIV-1 Tat-TAR interaction inhibitors
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Four new isoquinoline derivatives bearing guanidinium group or amino group-terminated side chain were synthesized to target the HIV-1 TAR element. Their abilities to bind TAR RNA and inhibit Tat-TAR RNA interaction were determined by CE analysis, a Tat-dependent HIV-1 LTR-driven CAT assay and SIV-induced syncytium evaluation.
- He, Meizi,Yuan, Dekai,Lin, Wei,Pang, Ruifang,Yu, Xiaolin,Yang, Ming
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- A chromone hydrazide Schiff base fluorescence probe with high selectivity and sensitivity for the detection and discrimination of human serum albumin (HSA) and bovine serum albumin (BSA)
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The discrimination and identification of human serum albumin (HSA) and bovine serum albumin (BSA) is very important, which is due to the vital roles of two SAs in biological and pharmaceutical research. Based on structural screening and docking calculation from a series of homologues, a coumarin Schiff base fluorescent probe 3-hydroxy-N′-((4-oxo-4H-chromen-3-yl)methylene)-2-naphthohydrazide (HCNH) has been designed and synthesized, which could effectively discriminate HSA and BSA. The probe HCNH exhibited superior sensitivity toward HSA and BSA with the detection limits of 10.62 nM and 16.03 nM in PBS solution, respectively. The binding mechanism of HCNH with SAs was studied by Job's plot analysis, SA destruction and displacement assay. Molecular docking and DFT methods were utilized to provide deep insight into the spatial conformation change of HCNH and binding sites in HSA/BSA. The conformation of HCNH was significantly influenced by the microenvironment provided by HSA and BSA, therefore its fluorescence emission was affected correspondingly. Non-toxic probe HCNH could be successfully used for fluorescence bio-imaging of HSA in cancer cells, which is significantly different from normal cells and favors the application in medical diagnosis.
- Yan, Xiao-Jing,Li, Zhe,Liu, Hai-Bo,Wang, Zhi-Gang,Fan, Jing,Xie, Cheng-Zhi,Li, Qing-Zhong,Xu, Jing-Yuan
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- Electrochemical Deoxygenation of N-Heteroaromatic N -Oxides
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An electrochemical method for the deoxygenation of N-heteroaromatic N -oxide to give the corresponding N-heteroaromatics has been developed. Several classes of N-heterocycles such as pyridine, quinoline, isoquinoline, and phenanthridine are tolerated. The electrochemical reactions proceed efficiently in aqueous solution without the need for transition-metal catalysts and waste-generating reducing reagents.
- Xu, H.-C.,Xu, P.
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supporting information
p. 1219 - 1221
(2019/06/08)
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- Design and Discovery of Novel Chiral Antifungal Amides with 2-(2-Oxazolinyl)aniline as a Promising Pharmacophore
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Inspired by established succinate dehydrogenase inhibitors (SDHIs), our continuing efforts toward the discovery of chiral antifungal amides turned to the optimization of their polar regions with 2-(2-oxazolinyl)aniline as a known pharmacophore. Scaffold hopping and bioactivity-guided convergent synthesis enabled the identification of promising antifungal categories. Fine tuning of the substituents and chirality furnished seven amides (1s, 1t, 2d, 2h, 2j, 3k, and 2l) as antifungal candidates, with EC50 values lower than 5 mg/L. The first investigation of chiral amides of acyclic acids as SDHIs was conducted, and compound 2d was selected as a promising candidate against Botrytis cinerea, with a preventative efficacy of up to 93.9% at 50 mg/L, which is better than that of boscalid. The different binding models between compounds with different configurations were simulated for compound 2d and its diastereoisomers. The benefits of synthetic accessibility and cost-effectiveness highlight the practical potential for compound 2d as a good alternative to known SDHI fungicides.
- Zhang, Lu,Li, Wei,Xiao, Taifeng,Song, Zehua,Csuk, René,Li, Shengkun
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p. 8957 - 8965
(2018/09/10)
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- Gene delivery system
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The invention discloses a preparation method of a gene nano-liposome carrier Isoquinoline-3-acyl-RGDV(IRV) and an IRV/STAT3-siRNA gene delivery system. The IRV/STAT3-siRNA gene delivery system is composed of liposome carriers IRV and STAT3-siRNA, protamine and calf thymus DNA in a proportion, and has slow release and targeting effects. The cell transfection efficiency, the in-vitro anti-tumor activity, and the gene silencing efficiency and a cell action mechanism on the mRNA level and the protein level of a compound are evaluated with the lung cancer A549 cell strain as a model, and the result shows the IRV/STAT3-siRNA gene delivery system has more excellent anti-tumor activity and gene silencing efficiency compared with control groups. According to the system, the anti-tumor activity of the IRV/STAT3-siRNA gene delivery system is evaluated with an S180 ascites tumor mouse as a model, and the result shows that a 100% IRV/STAT3-siRNA group has an anti-tumor effect.
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Paragraph 0088; 0089
(2017/10/27)
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- Imidazole-containing condensed tricyclic compound and application thereof
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The invention discloses an imidazole-containing condensed tricyclic compound adopting the structure as shown in the formula (I) or pharmaceutically acceptable salts, stereisomers or prodrug molecules thereof. The imidazole-containing condensed tricyclic compound has the IDO1 activity regulation function, can enhance T-cell activation through blocking immune checkpoints IDO1, is used for treating IDO1-mediated immunosuppression, and therefore, can become an effective medicine for treating malignant tumors. When used together with checkpoint protein anti-body drugs or other anti-cancer drugs, the imidazole-containing condensed tricyclic compound can enhance the anti-cancer effect. Meanwhile, the imidazole-containing condensed tricyclic compound has the potential of effectively treating IDO1 abnormity related immunosuppressive diseases and has a high application value.
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Paragraph 0383
(2018/03/01)
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- Development of a metal-free amine oxidation method utilizing DEAD chemistry
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Herein, we examine the oxidative abilities of azodicarboxylates for the conversion of amines to imines. This method provides access to synthetically useful imine intermediates including β-carbolines, quinazolines and N-heterocyclic carbene precursors. The ability to recover spent azodicarboxylate for regeneration and further use underscores the applicability and appeal of this protocol.
- Wang,Piva De Silva,Wiebe,Fehr,Davis
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p. 48848 - 48852
(2017/11/06)
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- Environment-responsive multivalent isoquinoline-3-carboxylic acid conjugate, and preparation method and application thereof
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The invention discloses an environment-responsive multivalent isoquinoline-3-carboxylic acid conjugate, and a preparation method and application thereof, belonging to the field of isoquinoline-3-carboxylic acid conjugates. According to the invention, 3,3'-dithiopropane diacid is used as a linking arm for coupling four isoquinoline-3-carboxylic acids with tris(2-aminoethyl)amine so as to form an isoquinoline derivative; multivalent synergism of a plurality of pharmacophores on a drug carrier is exerted on the lesion site of a tumor, so the antitumor activity of the antitumor drug is substantially improved; and through the environmental redox response of a disulfide bond to tumors, intelligent targeted release of the antitumor drug to a tumor part is realized, and toxicity of the antitumor drug to normal tissue is effectively reduced.
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Paragraph 0023; 0031; 0032
(2017/09/01)
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- Synthesis of isoquinoline-3-carboxylates and benzocyclobutanes via reaction of 2-amidoacrylate esters with arynes
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A mild and general method for the synthesis of a variety of 2-substituted isoquinoline 3-carboxylates and benzocyclobutanes from the reaction of 2-amidoacrylate esters with arynes has been developed. Georg Thieme Verlag Stuttgart.
- Blackburn, Tom,Ramtohul, Yeeman K.
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scheme or table
p. 1159 - 1164
(2009/04/05)
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- Solid-phase synthesis of indolecarboxylates using palladium-catalyzed reactions
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Polymer-supported, palladium-catalyzed cyclization reactions effectively synthesized indolecarboxylates. Palladium-catalyzed carbon - carbon bond-forming reactions of immobilized enaminoesters followed by transesterification yielded indole 2- or 3-carboxylates with various functional groups on the benzene ring. Indolecarboxylates were efficiently cyclized via an intramolecular palladium-catalyzed amination reaction of immobilized N-substituted dehydrohalophenylalanines, and immobilized N-acetyl-dehydroalanines were efficiently converted into indolecarboxylates via tandem Heck-amination reactions.
- Yamazaki, Kazuo,Nakamura, Yosuke,Kondo, Yoshinori
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p. 6011 - 6019
(2007/10/03)
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- Palladium-catalyzed tandem C,N-arylation of immobilized enamine for solid phase indole synthesis
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Intramolecular palladium-catalyzed N-arylation of immobilized dehydrohalophenylalaninate was found to proceed smoothly to form indolecarboxylates. The method was successfully combined with the Heck reaction to perform one pot indole synthesis via palladium-catalyzed tandem C,N-arylation reactions.
- Yamazaki, Kazuo,Nakamura, Yosuke,Kondo, Yoshinori
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p. 2137 - 2138
(2007/10/03)
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- Convenient Synthesis of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid and Its Derivatives as Doubly Constrained Nonproteinogenic Amino Acid Derivatives
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Three strategies for the synthesis of the novel, doubly constrained, 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and its derivatives were evaluated. Only cyclocondensation of the mono(triphenyl)phosphonium salt derived from 1,2-bis(bromomethyl)benzene with N-alkoxycarbonyloxamates in 1,2-dimethoxyethane in the presence of potassium carbonate and subsequent cyclopropanation with dimethylsulfoxonium methylide in dimethyl sulfoxide furnished suitable O-and N-protected derivatives of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in a convenient way. A detailed 2D DQF-COSY and 2D NOESY NMR analysis of the rotational isomerism of the latter bicyclic amino acid derivatives was performed. Various O- and N-protection protocols were worked out to afford access to a whole range of new derivatives of the title amino acid, suitable for peptide synthesis.
- Czombos, Jozsef,Aelterman, Wim,Tkachev, Alexey,Martins, Jose C.,Tourwe, Dirk,Peter, Antal,Toeth, Geza,Fueloep, Ferenc,De Kimpe, Norbert
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p. 5469 - 5475
(2007/10/03)
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- New synthesis of isoquinoline-3-carboxylates
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A new and general synthesis of methyl isoquinoline-3-carboxylates is described starting from aromatic 1,2-dialdehydes by reaction with protected phosphonoglycine derivatives. Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylates are obtained from 2-formylbenzoate derivatives. This new method allows the preparation of isoquinolines having electron-withdrawing groups on the benzene ring.
- Hiebl, Johann,Kollmann, Hermann,Levinson, Sidney H.,Offen, Priscilla,Shetzline, Steven B.,Badlani, Ruchi
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p. 7935 - 7938
(2007/10/03)
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- Intramolecular reactions of α-azidocinnamates with 4-substituted 1,3-dienes
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The synthesis of new 8,9-benzo-6-aza-bicyclo[3.2.2]nona-3.6.8-trienes 14 by intramolecular reaction of α-azidocinnamates 9 with alkyl- and phenylsubstituted ortho-butadienyl side chains is reported, as is the formation of the new 1-aza-2-carbomethoxy-7,8-benzo-tricyclo[4.30.02,9]nona-4,7-diene 15.
- Vogel,Delavier,Jones,Doring
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p. 1409 - 1412
(2007/10/02)
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- Vinyl Azides in Heterocyclic Synthesis. Part 6. Synthesis of Isoquinolines by Intramolecular Aza-Wittig Reaction
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Azidocinnamates containing ortho-carbonyl substituents are versatile intermediates for heterocyclic synthesis.Isoquinolines (8) and (9) are formed under mild neutral conditions by intramolecular aza-Wittig reactions of iminophosphoranes, readily derived f
- Hickey, Deirdre M. B.,MacKenzie, A. Roderick,Moody, Christopher J.,Rees, Charles W.
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p. 921 - 926
(2007/10/02)
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- Synthesis of Isoquinolines by Intramolecular Aza-Wittig Reaction
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Isoquinolines (3) and (5) are formed under mild neutral conditions by intramolecular aza-Wittig reactions of iminophosphoranes, readily derived from azides (1) and (4) with triethyl phosphite; the azafluoranthene (7) can also be prepared from the isolable
- Hickey, Deirdre M. B.,MacKenzie, A. Roderick,Moody, Christopher J.,Rees, Charles W.
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p. 776 - 777
(2007/10/02)
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- BIOMIMETIC APPROACH TO POTENTIAL BENZODIAZEPINE AGONISTS AND ANTAGONISTS
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A series of heterocycles have been prepared via the Pictet-Spengler reaction and several of these (β-carbolines 2-8, isoquinoline 11a and imidazopyridine derivative 16b) have been found to bind to the benzodiazepine receptor in vitro with moderate to high
- Cain, Michael,Guzman, Fil,Cook, James M.,Rice, Kenner C.,Skolnick, Phil
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p. 1003 - 1007
(2007/10/02)
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