4-Oxospiro[benzopyran-2,4'-piperidines] as class III antiarrhythmic agents. Pharmacological studies on 3,4-dihydro-1'-[2-(benzofurazan-5-yl)ethyl]-6-methanesulfonamidospiro[(2H)-1-benzopyran-2,4'-piperidin]-4-one (L-691,121)

Elliott, James M.; Hg, Selnick; Da, Claremon; Jj, Baldwin; Sa, Buhrow; Jw, Butcher; Cn, Habecker; Sw, King; Jj, Lynch; Bt, Phillips

doi:10.1021/jm00099a028

Cited by 24 publications

(13 citation statements)

References 5 publications

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“…One of the synthesized compounds 5 shows good in vivo potency (Scheme 2). 16 Similar antiarrhythmic agents are included in Figure 1. 17 was obtained by treatment of 1 with 12 followed by hydrolysis of the resultant product 13, hydrolysis of 13 to 14, and finally reduction of 14.…”

Section: Kabbe Condensationmentioning

confidence: 99%

“…13 The choice of pharmacophoric moieties is depended on their biological profiles, with the optimism that the resulting hybrid structures may show additional attractive pharmacological activities. 14,15 For example, as illustrated in Figure 1, the derivatives 10 of spirochromanones and spirochromanes are antiarrhythmic agents, 16,17 ACC inhibitors, 18 vanilloid receptor antagonists, 19 growth hormone secretagogues, 20 histamine receptor antagonists, 21 antiviral agents, 22 estrogen receptor modulators, 23 antineoplastic agents, 24 antifungal agents and DNA polymerase inhibitors. 25…”

Section: Introductionmentioning

confidence: 99%

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Recent Progress on Synthesis of Spirochromanone and Spirochromane Derivatives

Chakroborty¹,

Unnamatla²,

Panda³

et al. 2022

HETEROCYCLES

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Nature offers plenty of opportunities to the researchers of different communities to explore heterocyclic compounds. Among the various magic heterocyclic scaffolds, chromane and chromanone are the most privileged heterocycles due to their omnipresence in most value-added chemical entities. On the other hand, spirocyclic heterocyclic moieties offer unique three-dimensional frameworks which can fit into the cavity of the proteins, including enzymes, thereby enhancing the biological properties. Considering the remarkable significance of spirocyclic systems of chromanes and chromanones, various novel strategies such as Kabbe condensation, organocatalyzed reactions, oxa/sulfa-Michael-Aldol cascade reaction, oxa-Michael/addition and 1,3-dipolar cycloaddition, among others, have emerged to access this precious heterocyclic architecture in good to excellent yields. This review summarizes the synthesis of a variety of spirochromane and spirochromanone derivatives covering the literature from 1991-2020. CONTENTS1. Introduction 2.1. Synthesis of spirochromanones 2.1.1. Kabbe condensation 2.1.2. 1,3-Dipolar cycloaddition 2.1.3. Organocatalyzed reactions 2.1.4. Miscellaneous 2.2. Synthesis of spirochromanes 2.2.1. Organocatalyzed Michael addition 2.2.2. oxa-Michael/1,6-addition reactions 2.2.3. Metal catalyzed reactions 2.2.4. Miscellaneous 3. Conclusion 4. References

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Section: Kabbe Condensationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent Progress on Synthesis of Spirochromanone and Spirochromane Derivatives

Chakroborty¹,

Unnamatla²,

Panda³

et al. 2022

HETEROCYCLES

View full text Add to dashboard Cite

show abstract

“…162,[179][180][181] Chromones represent an attractive source of compounds of pharmacological interest due to their low toxicity. Furthermore, several spirochromanone derivatives have been reported to exhibit a wide range of biological activities: acetyl CoA carboxylase inhibitor, 182 antiarrhythmic activity, 183 delta-opioid receptor agonists for the treatment of pain. 184 A series of 2 0 -substituted-3 0 -methylpyro [cyclohexane-1,7 0furo [3,2-g] chroman]-5 0 (7 0 H)-one spiros (G9-G11) have been synthesized.…”

Section: Introductionmentioning

confidence: 99%

Spirocyclic derivatives as antioxidants: a review

et al. 2021

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“…Chromanones have many pharmaceutical applications, [ 1 ] in particular, 2,2‐dialkyl‐ and 2‐spiro‐chromanones are important heterocycles endowed wide range of bioactivity which include anti‐HIV, [ 2 ] antioxidant, [ 3 ] antidiabetic, [ 4 ] anti‐adhesion, [ 5 ] antihypertensive, [ 6,7 ] histamine receptor antagonist [ 8 ] and, consequently, have received considerable synthetic attention. [ 9 ] The most common methodology reported to prepare 2,2‐dialkyl‐substituted chroman‐4(1 H )‐ones involves the enamine‐catalyzed Kabbe condensation reaction of o ‐hydroxyacetophenones with alkyl ketones and pyrrolidine in refluxing toluene.…”

Section: Introductionmentioning

confidence: 99%