- Design, Synthesis and in vitro Evaluation of Indolotacrine Analogues as Multitarget-Directed Ligands for the Treatment of Alzheimer's Disease
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Novel indolotacrine analogues were designed, synthesized, and evaluated as potential drugs for the treatment of Alzheimer's disease. By using a multitarget-directed ligand approach, compounds were designed to act simultaneously as cholinesterase (ChE) and
- Benek, Ondrej,Soukup, Ondrej,Pasdiorova, Marketa,Hroch, Lukas,Sepsova, Vendula,Jost, Petr,Hrabinova, Martina,Jun, Daniel,Kuca, Kamil,Zala, Dominykas,Ramsay, Rona R.,Marco-Contelles, José,Musilek, Kamil
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Read Online
- Oseltamivir hydroxamate and acyl sulfonamide derivatives as influenza neuraminidase inhibitors
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Tamiflu, the ethyl ester form of oseltamivir carboxylic acid (OC), is the first orally available anti-influenza drug for the front-line therapeutic option. In this study, the OC-hydroxamates, OC-sulfonamides and their guanidino congeners (GOC)
- Hong, Bei-Tao,Chen, Chun-Lin,Fang, Jim-Min,Tsai, Keng-Chang,Wang, Shi-Yun,Huang, Wen-I,Cheng, Yih-Shyun E.,Wong, Chi-Huey
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Read Online
- Biosynthesis of [14C]-11-De-O-Methyltomaymycin, a Precursor of Radiolabelled Antibody Drug Conjugates
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Antibody drug conjugates (ADCs) are one of the most promising technologies to treat cancer as they combine the specificity of an antibody with the high potency of a cytotoxic molecule such as tomaymycin derivatives, which are DNA-interactive antitumor ant
- Aubert, Catherine,Lavisse, Mélanie,Roy, Sebastien
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p. 2424 - 2429
(2021/06/09)
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- Design, synthesis, antimicrobial evaluation, and molecular docking of novel chiral urea/thiourea derivatives bearing indole, benzimidazole, and benzothiazole scaffolds
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Urea/thiourea derivatives with heteroaromatic scaffolds such as indole, benzimidazole, and benzothiazole were designed, synthesized, and evaluated for their potential antimicrobial activity in vitro assays to establish against B. cereus, S. aureus, E. coli, and P. aeruginosa. Our results indicate that compounds are only active in gram-positive bacteria. Molecular docking studies were carried out for the most efficient compounds to understand the interactions with proteins involved in peptidoglycan synthesis. ADME calculations indicate that these compounds are more likely to be taken via the oral route. In summary, these findings may contribute to the design and development of candidates for more effective therapeutics in biological systems.
- Lafzi, Ferruh,Kilic, Deryanur,Yildiz, Melike,Saracoglu, Nurullah
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- Disparate Catalytic Scaffolds for Atroposelective Cyclodehydration
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Catalysts that control stereochemistry are prized tools in chemical synthesis. When an effective catalyst is found, it is often explored for other types of reactions, frequently under the auspices of different mechanisms. As successes mount, a unique cata
- Kwon, Yongseok,Li, Junqi,Reid, Jolene P.,Crawford, Jennifer M.,Jacob, Roxane,Sigman, Matthew S.,Toste, F. Dean,Miller, Scott J.
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supporting information
p. 6698 - 6705
(2019/05/06)
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- Regio- and chemoselective n-1 acylation of indoles: Pd-catalyzed domino cyclization to afford 1,2-fused tricyclic indole scaffolds
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A concise method for the synthesis of 1,2-fused tricyclic indole scaffolds by domino cyclization involving a Pd-catalyzed Sonogashira coupling, indole cyclization, regio- and chemoselective N-1 acylation, and 1,4-Michael addition is reported. This method
- Liu, Yongxian,Huang, Yuanqiong,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 5337 - 5340
(2015/03/30)
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- Self-induced stereoselective in situ trifluoromethylation: Preparation of spiro[indoline-3,3′-quinoline] via palladium-catalyzed cascade reaction
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An efficient method to prepare 1′H-spiro[indoline-3,3′- quinoline]-2′,4′-diones and their trifluoromethylated products was developed via a palladium-catalyzed Sonogashira coupling/Wacker-type oxypalladation/cyclization cascade reaction. The amount of wate
- Song, Hongjian,Liu, Yongxian,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 3240 - 3243
(2014/07/08)
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- Radical cyclizations of cyclic ene sulfonamides occur with β-elimination of sulfonyl radicals to form polycyclic imines
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Radical cyclizations of cyclic ene sulfonamides provide stable bicyclic and tricyclic aldimines and ketimines in good yields. Depending on the structure of the precursor, the cyclizations occur to provide fused and spirocyclic imines with five-, six-, and seven-membered rings. The initial radical cyclization produces an α-sulfonamidoyl radical that undergoes elimination to form the imine and a phenylsulfonyl radical. In a related method, 3,4-dihydroquinolines can also be produced by radical translocation reactions of N-(2- iodophenylsulfonyl)tetrahydroiso-quinolines. In either case, very stable sulfonamides are cleaved to form imines (rather than amines) under mild reductive conditions.
- Zhang, Hanmo,Hay, E. Ben,Geib, Steven J.,Curran, Dennis P.
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supporting information
p. 16610 - 16617
(2013/12/04)
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- An efficient, microwave-assisted, one-pot synthesis of indoles under Sonogashira conditions
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A microwave-assisted, one-pot, three-component coupling reaction for the synthesis of indoles has been developed. The reaction is carried out in two steps under standard Sonogashira coupling conditions from an N-substituted/N,N-disubstituted 2-iodoaniline and a terminal alkyne, followed by the addition of acetonitrile and an aryl iodide. A variety of polysubstituted indoles have been prepared in moderate to excellent yields using the present method.
- Chen, Yu,Markina, Nataliya A.,Larock, Richard C.
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experimental part
p. 8908 - 8915
(2009/12/08)
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- Iron-catalyzed aryl-aryl cross-coupling reaction tolerating amides and unprotected quinolinones
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The iron(III)-catalyzed cross-coupling reaction between functionalized arylcopper reagents and aromatic iodides bearing an amide function or an unprotected quinolinone leads smoothly to polyfunctionalized biphenyls in excellent yields due to an intramolec
- Kofink, Christiane C.,Blank, Benoit,Pagano, Sandro,Goetz, Nadine,Knochel, Paul
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p. 1954 - 1956
(2008/02/07)
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- FUSED BICYCLOHETEROCYCLE SUBSTITUTED QUINUCLIDINE DERIVATIVES
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Compounds of formula (I) wherein n is 0, 1, or 2; A is N or N+-O-; X is O, S, -NH-, and -N-alkyl-; Ar1 is a 6-membered aromatic ring; and Ar2 is a fused bicycloheterocycle. The compounds are useful in treating conditions or disorders prevented by or ameliorated by a7 nAChR ligands. Also disclosed are pharmaceutical compositions having compounds of formula (I) and methods for using such compounds and compositions.
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Page/Page column 55
(2010/11/08)
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- Acetonitrile-mediated synthesis of 2,4-dichloroquinoline from 2-ethynylaniline and 2,4-dichloroquinazoline from anthranilonitrile
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2,4-Dichloroquinolines and 2,4-dichloroquinazolines were synthesized from 2-ethynylanilines and anthranilonitriles, respectively, using diphosgene in acetonitrile and heating at 130 °C or 150 °C for 12 hours. This reaction was applied to the synthesis of 4,6-dichloropyrazolo[3,4-d]pyrimidine (dichloro-9H-isopurine). The postulated mechanism is also described. Georg Thieme Verlag Stuttgart.
- Lee, Jae Hak,Lee, Byoung Se,Shin, Hyunik,Nam, Do Hyun,Chi, Dae Yoon
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- Fused bicycloheterocycle substituted quinuclidine derivatives
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Compounds of formula (I) wherein n is 0, 1, or 2; X is O, S, —NH—, and —N-alkyl-; Ar1 is a 6-membered aromatic ring; and Ar2 is a fused bicycloheterocycle. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions having compounds of formula (I) and methods for using such compounds and compositions.
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Page/Page column 21
(2010/02/12)
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- Fused bicycloheterocycle substituted quinuclidine derivatives
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Compounds of formula (I) wherein n is 0, 1, or 2; A is N or N+—O?; X is O, S, —NH—, and —N-alkyl-; Ar1 is a 6-membered aromatic ring; and Ar2 is a fused bicycloheterocycle. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions having compounds of formula (I) and methods for using such compounds and compositions.
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Page/Page column 24
(2010/02/12)
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- Fused bicycloheterocycle substituted quinuclidine derivatives
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Compounds of formula (I) wherein n is 0, 1, or 2; A is N or N+—O—; X is O, S, —NH—, and —N-alkyl-; Ar1 is a 6-membered aromatic ring; and Ar2 is a fused bicycloheterocycle. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions having compounds of formula (I) and methods for using such compounds and compositions.
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- Solid-phase syntheses of furopyridine and furoquinoline systems
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Syntheses of 2-substituted furo[3,2-b]pyridines and furo[3,2-h]quinolines have been achieved for the first time in the solid-phase mode. The central enabling steps involved concomitant deprotection/cyclization promoted by the mild base K2COsub
- Cironi, Pablo,Tulla-Puche, Judit,Barany, George,Albericio, Fernando,Alvarez, Mercedes
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p. 1405 - 1408
(2007/10/03)
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- Synthesis of medium ring heterocycles using an intramolecular Heck reaction
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(Equation Presented) Historically, general convergent syntheses of medium ring heterocycles have been difficult to develop. Herein, we describe the synthesis of five classes of heterocycles: dihydrodibenzo[b,f]azepine, -oxocine, and -thiocine and dibenzo[b,f]azepine and -oxepine using a strategy of alkylation followed by highly selective intramolecular Heck arylation reaction. The hetero-tricyclic compounds were available in only two steps starting from commercially available starting materials.
- Arnold, Leggy A.,Luo, Wenchen,Guy, R. Kiplin
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p. 3005 - 3007
(2007/10/03)
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- Synthesis of 2-quinolones via palladium-catalyzed carbonylative annulation of internal alkynes by N-substituted o-iodoanilines
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The palladium-catalyzed annulation of internal alkynes by N-substituted o-iodoanilines under 1 atm of carbon monoxide results in the formation of 3,4-disubstituted 2-quinolones. The nature of the substituent on the nitrogen is crucial to obtaining high yields of 2-quinolones. The best results are obtained using alkoxycarbonyl, p-tolylsulfonyl, and trifluoroacetyl substituents. The nitrogen substituent is lost during the course of the reaction resulting in the formation of N-unsubstituted 2-quinolones. A variety of internal alkynes, bearing alkyl, aryl, heteroaryl, hydroxyl, and alkoxyl substituents, are effective in this process. Electron-rich and electron-poor N-substituted o-iodoanilines, as well as heterocyclic analogues, can be employed as annulating agents.
- Kadnikov, Dmitry V.,Larock, Richard C.
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p. 6772 - 6780
(2007/10/03)
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- Sonogashira coupling and cyclization reactions on alumina: A route to aryl alkynes, 2-substituted-benzo[b]furans and 2-substituted-indoles
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A solventless, microwave-enhanced Sonogashira coupling reaction of aromatic iodides with terminal alkynes on potassium fluoride doped alumina in the presence of palladium powder, cuprous iodide, and triphenylphosphine has been developed. The reaction can be utilized to prepare aryl alkynes in excellent yields. The coupling of o-iodophenol with terminal alkynes leads to the formation 2-substituted-benzo[b]furans. Whereas the coupling of o-iodoanilines with terminal alkynes generates indole products. An in situ desilylation reaction was also developed.
- Kabalka, George W.,Wang, Lei,Pagni, Richard M.
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p. 8017 - 8028
(2007/10/03)
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- INDOLE DERIVATIVES
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Compounds of the formula STR1 wherein the substituents are as defined in the description and the pharmaceutically acceptable salts thereof are new. These compounds are useful psychotherapeutics and are potent serotonin (5-HT 1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting antihypertensives and vasodilators. A process for forming indoles by transition metal catalyzed cyclization of a dihalogenated intermediate.
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- INDOLE DERIVATIVES
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Compounds of the formula STR1 wherein R 1, R 2, R. sub.3, X and n are as defined in the claims and the pharmaceutically acceptable salts thereof are new. These compounds are useful psychotherapeutics and are potent serotonin (5-HT 1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting hypertensives and vasodilators. A process for forming indoles by transition metal catalyzed cyclization of dihalogenated intermediate is also disclosed.
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- INDOLE DERIVATIVES
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Compounds of the formula STR1 wherein n is 0, 1, or 2; X is hydrogen, chlorine, bromine or iodine; R 1 is hydrogen; R 3 is selected from hydrogen and C 1 to C 6 linear or branched alkyl; and R 2 is as defined in the specification and the pharmaceutically acceptable salts thereof are useful psychotherapeutics and are potent serotonin (5-HT 1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting antihypertensives and vasodilators. A process for forming indoles by transition metal catalyzed cyclization of a dihalogenated intermediate is also disclosed.
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- INDOLE DERIVATIVES
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Compounds of the formula STR1 wherein R 1, R 2, R. sub.3, X and n are as defined in the claims and the pharmaceutically acceptable salts thereof are new. These compounds are useful psychotherapeutics and are potent serotonin (5-HT 1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting hypertensives and vasodilators. A process for forming indoles by transition metal catalyzed cyclization of dihalogenated intermediate is also disclosed.
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- INDOLE DERIVATIVES
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Compounds of the formula STR1 wherein R 1, R 2, R. sub.3, X and n are as defined in the claims and the pharmaceutically acceptable salts thereof are new. These compounds are useful psychotherapeutics and are potent serotonin (5-HT 1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting hypertensives and vasodilators. A process for forming indoles by transition metal catalyzed cyclization of dihalogenated intermediate is also disclosed.
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- Stereoselective Synthesis of Exocyclic Allylsilanes by Intramolecular Reductive Heck Cyclisation of Propargylsilanes
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The stereoselective palladium-catalysed synthesis of the heterocycles 13-15 with a (Z)-exocyclic allylsilane moiety is described.Alkylation of the secondary amides 5a, 5b, 9a, and 9b and the phenol 11 containing an iodoaryl moiety with the propargyl iodid
- Tietze, Lutz F.,Schimpf, Ralph
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p. 2235 - 2240
(2007/10/02)
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