Triazole-Containing Isothiazolidine 1,1-Dioxide Library Synthesis: One-Pot, Multi-Component Protocols for Small Molecular Probe Discovery

Rolfe, Alan; Painter, Thomas O.; Asad, Naeem; Hur, Moon Young; Jeon, Kyu Ok; Brzozowski, Marek; Klimberg, Sarra V.; Porubsky, Patrick; Neuenswander, Benjamin; Lushington, Gerald H.; Santini, Conrad; Hanson, Paul R.

doi:10.1021/co200093c

Cited by 12 publications

(8 citation statements)

References 38 publications

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“…Absorption, distribution, metabolism and excretion (ADME) properties were calculated by using the Volsurf program [ 39 ]. Cartesian grid-based chemical diversity analysis was performed according to the method described previously [ 40 ], by using standard H-aware 3D BCUT descriptors comparing against the MLSMR screening set (ca. 7/2010; ~330,000 unique chemical structures).…”

Section: Resultsmentioning

confidence: 99%

Exploring chemical diversity via a modular reaction pairing strategy

Loh

Yoon²,

Samarakoon³

et al. 2012

Beilstein J. Org. Chem.

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SummaryThe efficient synthesis of an 80-member library of unique benzoxathiazocine 1,1-dioxides by a microwave-assisted, intermolecular nucleophilic aromatic substitution (SNAr) diversification pathway is reported. Eight benzofused sultam cores were generated by means of a sulfonylation/SNAr/Mitsunobu reaction pairing protocol, and subsequently diversified by intermolecular SNAr with ten chiral, non-racemic amine/amino alcohol building blocks. Computational analyses were employed to explore and evaluate the chemical diversity of the library.

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Section: Resultsmentioning

confidence: 99%

Exploring chemical diversity via a modular reaction pairing strategy

Loh

Yoon²,

Samarakoon³

et al. 2012

Beilstein J. Org. Chem.

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“…Hanson et al developed two libraries of triazole‐containing sultams through one‐pot click‐aza‐Michael or click‐oligomeric alkyl carbodiimide esterification protocols in which the sultam core was prepared by metathesis of N ‐allylethenesulfonamide derivatives in the presence of [(PCy 3 ) 2 (Cl) 2 Ru=CHPh] catalyst in CH 2 Cl 2 …”

Section: Synthesis Of Sultamsmentioning

confidence: 99%

Sultams: Recent Syntheses and Applications

Debnath¹,

Mondal²

2018

Eur J Org Chem

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Sultams are very important scaffolds both in medicinal chemistry and in synthetic organic chemistry. Very important methodologies for the asymmetric and non‐asymmetric synthesis of sultams, including asymmetric synthesis with memory of chirality (MOC), have recently been developed. Nowadays sultams are tremendously widely applied both in the medicinal field and in the synthetic field for the synthesis of different natural and non‐natural heterocycles. This review covers the recent development (2011–June 2017) of powerful methodologies for the synthesis of sultams and their applications in various fields during this period. A critical view of the mechanisms of the developed methodologies together with the scope and limitations of these methods add an extra dimension to the text.

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“…[163] Due to the anti-HIV and antibacterial activity of baminosultams and their corresponding sulfonate analogues, much attention has been given for devising synthetic methods for the preparation of sultam derivatives. This concept bears an enormous potential for the creation of novel combinations of multi-component reactions.…”

Section: Multiple Mcrs Coupled With Cuaacmentioning

confidence: 99%

“…This concept bears an enormous potential for the creation of novel combinations of multi‐component reactions. In a one‐pot CuAAC‐aza‐Michael or CuAAC‐aza‐Michael‐OACC (oligomeric alkyl carbodiimide)‐esterification sequence, two libraries of triazole‐containing isothiazolidine 1,1‐dioxides 90 and 91 have been established (Scheme ) 163…”

Section: Multiple Mcrs Coupled With Cuaacmentioning

confidence: 99%

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

2015

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The copper-catalyzed alkyne-azide cycloaddition (CuAAC) is a highly versatile, regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles under mild reaction conditions and has found numerous applications in medicinal, bioorganic, and materials chemistry in the past one and a half decades. By virtue of the enormous tolerance for functional groups and the mild reaction conditions, CuAAC has become increasingly important in combination with multicomponent reactions (MCR), either in a domino or in a consecutive fashion. While the majority of CuAAC-based MCR are founded on the in situ or en route generation of azides, one-pot generation of alkynes and the concatenation with other MCR are rapidly catching up and novel sequences for efficient one-pot syntheses of triazole-based structures in a multicomponent fashion are constantly evolving. This review summarizes important contributions of CuAAC-based MCR including MCRtype applications in polymer science.

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Triazole-Containing Isothiazolidine 1,1-Dioxide Library Synthesis: One-Pot, Multi-Component Protocols for Small Molecular Probe Discovery

Cited by 12 publications

References 38 publications

Exploring chemical diversity via a modular reaction pairing strategy

Exploring chemical diversity via a modular reaction pairing strategy

Sultams: Recent Syntheses and Applications

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

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