Synthesis and antinociceptive activity of 1-methylpiperidylidene-2-(pyridyl)sulfonamides and related dihydropyridyl analogs

Buolamwini, J K; Knaus, EE

doi:10.1016/0223-5234(93)90012-4

Cited by 8 publications

(3 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, regioisomeric mixtures were obtained in the addition of Grignard reagents to the Nbenzoylpyridinium salt of a pyridin-3-yl sulfonamide. 17 In the present study, reductive deoxygenation of 3-azatricyclo[2.2.1.0 2,6 ]heptan-5-ols 9 [bearing an aryl or methoxy substituent in the 7-position and an electron withdrawing group (sulfone or ester) at C-1] is shown to provide a regiospecific route to 2,5-disubstituted 1,2-dihydropyridines 12. As the precursor to epoxide 8 (the cycloadduct of N-Boc pyrrole and tosyl ethyne) is available as either enantiomer, 18 then the potential for accessing enantiopure 1,2-dihydropyridines 12 also exists.…”

Section: Methodsmentioning

confidence: 98%

Radical Deoxygenation of 3-Azatricyclo[2.2.1.0^2,6]heptan-5-ols to 1,2-Dihydropyridines

Hodgson¹,

Jones²,

Maxwell³

et al. 2005

Synlett

View full text Add to dashboard Cite

Radical deoxygenations of 7-alkyl-1-tosyl-3-azatricyclo[2.2.1.0 2,6 ]heptan-5-ols 9 (R = alkyl) give 7-alkyl-4-tosyl-2-azabicyclo[2.2.1]hept-5-enes 10, whereas 7-aryl-1-tosyl-3-azatricyclo[2.2.1.0 2,6 ]heptan-5-ols 9 (R = aryl) give 2-aryl-5-tosyl-1,2-dihydropyridines 12.Radical cyclisations and rearrangements constitute powerful methodology for the synthesis of ring systems. 1 Radical rearrangements in nortricyclyl (tricyclo[2.2.1.0 2,6 ]heptanyl) and norbornenyl (bicyclo[2.2.1]heptenyl) systems are well-known, usually leading to mixtures of tricyclic and bicyclic products. For example, radical-induced reductions of nortricyclyl bromide 1 and norbornenyl bromide 2 are known to give the same mixture of nortricyclene 3 and norbornene 4 (3:4, ca. 40:60; Scheme 1). 2 Scheme 1Recently, during the development of novel analgesics related to epibatidine, we showed that radical deoxygenation of 7-azanortricyclanols 5 selectively gave 6-substituted 2-azabicyclo[2.2.1]hept-5-enes 7, even when R is potentially radical stabilising (e.g. aryl, Scheme 2). 3 The origin of the selectivity in this rearrangement is probably the stabilisation afforded to the intermediate radical 6 by the a-nitrogen. 4 In the present communication we report on studies originally designed to broaden the scope of the above strategy to give differently substituted 2-azabicyclo[2.2.1]hept-5-enes, but which have also led to an extended radical rearrangement process to give 1,2-dihydropyridines.Epoxide 8 (readily available in two steps from N-Boc pyrrole) 5 underwent exo-selective attack at the a,b-unsaturated sulfone functionality with a variety of Grignard reagents, organolithiums, and MeOLi 6 to give the corresponding substituted 7-azanortricyclanols 9 in good yields (72-96%, Scheme 3). In the case of 7-azanortricyclanol 9 (R = 4-MeOC 6 H 4 ) the structural assignment was supported by X-ray crystallographic analysis. 7 Subsequent radical deoxygenation 8 of alkyl-substituted 7-azanortricyclanols 9 (R = Me, i-Pr) using Bu 3 SnH (2 equiv) gave the anticipated 2-azabicyclo[2.2.1]heptenes 10. 9

show abstract

Section: Methodsmentioning

confidence: 98%

Radical Deoxygenation of 3-Azatricyclo[2.2.1.0^2,6]heptan-5-ols to 1,2-Dihydropyridines

Hodgson¹,

Jones²,

Maxwell³

et al. 2005

Synlett

View full text Add to dashboard Cite

show abstract

“…[18][19][20][21][22][23][24] Sulfonamide also showed broad spectrum of pharmacological properties such as antibacterial, antifungal, anticandidal, antinociceptive, anticancer and anti-inflammatory activities. [25][26][27][28][29][30] The quinazolin-4(3H)-one incorporated with different type of aryl as well as heteryl linkers, showed wide range of pharmacological applications. In the present work we have synthesized quinazolin-4(3H)-one incorporated with 4-thiazolidinone and evaluated its in vitro antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Quinazolin‐4(3H)‐ones Incorporating Sulfonamido‐4‐thiazolidinone

Patel

2010

Chin. J. Chem.

View full text Add to dashboard Cite

Some new derivatives 7-chloro-2-[2-(2,6-dichlorophenyl)amino]benzyl-3-[4-(2-substituted phenyl-4-oxothiazolidin-3-yl)phenyl]sulfonamido-quinazolin-4(3H)-ones 5a -5l were synthesized from 2-[2-(2,6-dichlorophenyl)amino]phenyl acetic acid via acid chloride, benzoxazinone, amino quinazolin-4(3H)-one and Schiff base formation. The synthesized compounds were screened for in vitro antibacterial and antifungal activities by broth micro dilution method. Some of the Schiff base as well as 4-thiazolidinone derivatives showed promising antibacterial activity while pronounced antifungal activity was observed against C. albicans.

show abstract

“…Scheme illustrates the rapid “pre-assembly” of photoprecursor 7b from aminotetralone 3 and alanine-derived pyrrole 4b and its photoinduced conversion to pentacyclic enamine 10b . Without additional purification, 10b is reacted with toluenesulfonyl azide yielding cyclic N -sulfonyl amidine 11b (the ORTEP drawing of its X-ray structure is shown) …”

mentioning

confidence: 99%

Photoassisted Synthesis of Enantiopure Alkaloid Mimics Possessing Unprecedented Polyheterocyclic Cores

2013

View full text Add to dashboard Cite

Enantiopure alkaloid mimics are synthesized via high yielding intramolecular cycloadditions of photogenerated azaxylylenes tethered to pyrroles, with further growth of molecular complexity via post-photochemical transformations of primary photoproducts. This expeditious access to structurally unprecedented polyheterocyclic cores is being developed in the context of diversity-oriented synthesis, as the modular design allows for rapid “pre-assembly” of diverse photoprecursors from simple building blocks/diversity inputs.

show abstract

Synthesis and antinociceptive activity of 1-methylpiperidylidene-2-(pyridyl)sulfonamides and related dihydropyridyl analogs

Cited by 8 publications

References 12 publications

Radical Deoxygenation of 3-Azatricyclo[2.2.1.0^2,6]heptan-5-ols to 1,2-Dihydropyridines

Radical Deoxygenation of 3-Azatricyclo[2.2.1.0^2,6]heptan-5-ols to 1,2-Dihydropyridines

Synthesis and Antimicrobial Activity of Quinazolin‐4(3H)‐ones Incorporating Sulfonamido‐4‐thiazolidinone

Photoassisted Synthesis of Enantiopure Alkaloid Mimics Possessing Unprecedented Polyheterocyclic Cores

Contact Info

Product

Resources

About

Synthesis and antinociceptive activity of 1-methylpiperidylidene-2-(pyridyl)sulfonamides and related dihydropyridyl analogs

Cited by 8 publications

References 12 publications

Radical Deoxygenation of 3-Azatricyclo[2.2.1.02,6]heptan-5-ols to 1,2-Dihydropyridines

Radical Deoxygenation of 3-Azatricyclo[2.2.1.02,6]heptan-5-ols to 1,2-Dihydropyridines

Synthesis and Antimicrobial Activity of Quinazolin‐4(3H)‐ones Incorporating Sulfonamido‐4‐thiazolidinone

Photoassisted Synthesis of Enantiopure Alkaloid Mimics Possessing Unprecedented Polyheterocyclic Cores

Contact Info

Product

Resources

About

Radical Deoxygenation of 3-Azatricyclo[2.2.1.0^2,6]heptan-5-ols to 1,2-Dihydropyridines

Radical Deoxygenation of 3-Azatricyclo[2.2.1.0^2,6]heptan-5-ols to 1,2-Dihydropyridines