Combining a Click–Multicomponent Reaction: One-Pot Synthesis of 1,2,3-Triazol-4-ylmethyl 3-Amino-5,10-dihydro-5,10-dioxo-1<i>H</i>-pyrazolo[1,2-<i>b</i>]phthalazine-2-carboxylate Derivatives

Dabiri, Minoo; MaGee, David I.; Salehi, Peyman; Torkian, Laleh; Fakharian, Mahsa; Donahue, Jordan

doi:10.1080/00397911.2014.888080

“…A four‐component sequence involving the reaction of aromatic aldehydes, azides, prop‐2‐ynyl 2‐cyanoacetate, and phthalhydrazide has been developed for the synthesis of 1 H ‐pyrazolo[1,2‐ b ]phthalazine skeleton 101 via one‐pot reaction involving aldol condensation‐CuAAC‐Michael addition‐intramolecular cyclization 174. This reaction sequence establishes its efficacy by achieving highly complex molecular diversity in good yields using simple starting materials and recyclable ionic liquid as reaction medium (Scheme ).…”

Section: Multiple Mcrs Coupled With Cuaacmentioning

confidence: 99%

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

Hassan

¹

,

Müller

²

2015

View full text Add to dashboard Cite

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.

show abstract

Orthogonal Persulfide Generation through Precision Tools Provides Insights into Mitochondrial Sulfane Sulfur

Manna,

Agrawal,

Yadav

et al. 2024

Angewandte Chemie

0

View full text Add to dashboard Cite

The sulfane sulfur pool, comprised of persulfide (RS‐SH) and polysulfide (RS‐SnH) derived from hydrogen sulfide (H2S), has emerged as a major player in redox biochemistry. Mitochondria, besides energy generation, serve as significant cellular redox hubs, mediate stress response and cellular health. However, the effects of endogenous mitochondrial sulfane sulfur (MSS) remain largely uncharacterized as compared with their cytosolic counterparts, cytosolic sulfane sulfur (CSS). To investigate this, we designed a novel artificial substrate for mitochondrial 3‐mercaptopyruvate sulfurtransferase (3‐MST), a key enzyme involved in MSS biosynthesis. Using cells expressing a mitochondrion‐localized persulfide biosensor, we demonstrate this tool’s ability to selectively enhance MSS. While H2S was previously known to suppress human immunodeficiency virus (HIV‐1), we found that MSS profoundly affected the HIV‐1 life cycle, mediating viral reactivation from latency. Additionally, we provide evidence for the role of the host’s mitochondrial redox state, membrane potential, apoptosis, and respiration rates in managing HIV‐1 latency and reactivation. Together, dynamic fluctuations in the MSS pool have a significant and possibly conflicting effect on HIV‐1 viral latency. The precision tools developed herein allow for orthogonal generation of persulfide within both mitochondria and the cytosol and will be useful in interrogating disease biology.

show abstract

Orthogonal Persulfide Generation through Precision Tools Provides Insights into Mitochondrial Sulfane Sulfur

Manna,

Agrawal,

Yadav

et al. 2024

Angew Chem Int Ed

1

0

View full text Add to dashboard Cite

The sulfane sulfur pool, comprised of persulfide (RS‐SH) and polysulfide (RS‐SnH) derived from hydrogen sulfide (H2S), has emerged as a major player in redox biochemistry. Mitochondria, besides energy generation, serve as significant cellular redox hubs, mediate stress response and cellular health. However, the effects of endogenous mitochondrial sulfane sulfur (MSS) remain largely uncharacterized as compared with their cytosolic counterparts, cytosolic sulfane sulfur (CSS). To investigate this, we designed a novel artificial substrate for mitochondrial 3‐mercaptopyruvate sulfurtransferase (3‐MST), a key enzyme involved in MSS biosynthesis. Using cells expressing a mitochondrion‐localized persulfide biosensor, we demonstrate this tool’s ability to selectively enhance MSS. While H2S was previously known to suppress human immunodeficiency virus (HIV‐1), we found that MSS profoundly affected the HIV‐1 life cycle, mediating viral reactivation from latency. Additionally, we provide evidence for the role of the host’s mitochondrial redox state, membrane potential, apoptosis, and respiration rates in managing HIV‐1 latency and reactivation. Together, dynamic fluctuations in the MSS pool have a significant and possibly conflicting effect on HIV‐1 viral latency. The precision tools developed herein allow for orthogonal generation of persulfide within both mitochondria and the cytosol and will be useful in interrogating disease biology.

show abstract

Combining a Click–Multicomponent Reaction: One-Pot Synthesis of 1,2,3-Triazol-4-ylmethyl 3-Amino-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carboxylate Derivatives

Abstract: Copies of 1 H NMR and 13 C NMR spectra of compounds.

Cited by 9 publications

References 25 publications

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

Orthogonal Persulfide Generation through Precision Tools Provides Insights into Mitochondrial Sulfane Sulfur

Orthogonal Persulfide Generation through Precision Tools Provides Insights into Mitochondrial Sulfane Sulfur

Contact Info

Product

Resources

About