Indoles — A promising scaffold for drug development

Sravanthi, T. V.; Manju, S. L.

doi:10.1016/j.ejps.2016.05.025

Cited by 532 publications

(232 citation statements)

References 53 publications

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“…Furthermore, indoles serve as promising scaffolds for drug development due to their antibacterial, anticancer, anti-oxidant, anti-inflammatory, anti-diabetic, antiviral, antiproliferative, and antituberculosis activities 56, 57 . The present study is the first to suggest the potential use of iodoindoles as antiparasitics or anthelmintics.…”

Section: Discussionmentioning

confidence: 99%

Assessments of iodoindoles and abamectin as inducers of methuosis in pinewood nematode, Bursaphelenchus xylophilus

Rajasekharan

Lee

Ravichandran

2017

Sci Rep

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Bursaphelenchus xylophilus is a quarantined migratory endoparasite known to cause severe economic losses in pine forest ecosystems. The study presents the nematicidal effects of halogenated indoles on B. xylophilus and their action mechanisms. 5-Iodoindole and abamectin (positive control) at low concentration (10 µg/mL) presented similar and high nematicidal activities against B. xylophilus. 5-Iodoindole diminished fecundity, reproductive activities, embryonic and juvenile lethality and locomotor behaviors. Molecular interactions of ligands with invertebrate-specific glutamate gated chloride channel receptor reinforced the notion that 5-iodoindole, like abamectin, rigidly binds to the active sites of the receptor. 5-Iodoindole also induced diverse phenotypic deformities in nematodes including abnormal organ disruption/shrinkage and increased vacuolization. These findings suggest the prospective role of vacuoles in nematode death by methuosis. Importantly, 5-iodoindole was nontoxic to two plants, Brassica oleracea and Raphanus raphanistrum. Henceforth, the study warrants the application of iodoindoles in ecological environments to control the devastating pine destruction by B. xylophilus.

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Section: Discussionmentioning

confidence: 99%

Assessments of iodoindoles and abamectin as inducers of methuosis in pinewood nematode, Bursaphelenchus xylophilus

Rajasekharan

Lee

Ravichandran

2017

Sci Rep

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“…[34] Standard optimization varying the solventa nd electrophiles revealed that NIS was superior compared to NBS or NCS and THF was a better solventc ompared to acetonitrile or methanol (Scheme 4). [34] Standard optimization varying the solventa nd electrophiles revealed that NIS was superior compared to NBS or NCS and THF was a better solventc ompared to acetonitrile or methanol (Scheme 4).…”

mentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of Heterobiaryls through 1,2‐Migration of Boronate Complex

Paul

Das

Manna

et al. 2020

Chemistry A European J

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The synthesis of a diverse range of heterobiaryls has been achieved by a transition‐metal‐free sp2–sp2 cross‐coupling strategy using lithiated heterocycle, aryl or heteroaryl boronic ester and an electrophilic halogen source. The construction of heterobiaryls was carried out through electrophilic activation of the aryl–heteroaryl boronate complex, which triggered 1,2‐migration from boron to the carbon atom. Subsequent oxidation of the intermediate boronic ester afforded heterobiaryls in good yield. A comprehensive 11B NMR study has been conducted to support the mechanism. The cross coupling between two nucleophilic cross coupling partners without transition metals reveals a reliable manifold to procure heterobiaryls in good yields. Various heterocycles like furan, thiophene, benzofuran, benzothiophene, and indole are well tolerated. Finally, we have successfully demonstrated the gram scale synthesis of the intermediates for an anticancer drug and OLED material using our methodology.

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“…[6b] Earlier DFT calculations on am ixed-ligand [Au 11 (PPh 3 ) 7 (NHC i-Pr )Cl 2 ]Cl cluster have shown that the Au-carbene bond can be stronger than Auphosphine bond by up to 0.9 eV.T his explains also the observed superior thermal stability of 1 over 2 in this work. [20] Thec atalytic reaction was conducted by adding 1.5 mmol %(based on Au)of1 to asolution of alkynyl amine in organic solvents.A se nvisioned, 1.5 mmol %c atalyst (calculated based on Au atom) succeeded in accelerating the cycloisomerization reaction of N-(2-ethylnylphenyl)-4methylbenzenesulfonamidet o1 -tosyl-1H-indole at 25 8 8Ci n 10 h( Supporting Information, Table S2, entry 1). Indoles are important heterocycles which are broadly used in material science and biology.…”

Section: Angewandte Chemiementioning

confidence: 99%

Highly Robust but Surface-Active: N-Heterocyclic Carbene-Stabilized Au25 Nanocluster as a Homogeneous Catalyst

Shen¹,

Deng²,

Kaappa³

et al. 2019

Preprint

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Surface organic ligands playac ritical role in stabilizing atomically precise metal nanoclusters in solutions. However,itisstill challenging to prepare highly robust ligated metal nanoclusters that are surface-active for liquid-phase catalysis without any pre-treatment. Now,a nN -heterocyclic carbene-stabilized Au 25 nanocluster with high thermal and air stabilities is presented as ah omogenous catalyst for cycloisomerization of alkynyl amines to indoles.T he nanocluster, characterized as [Au 25 ( i Pr 2 -bimy) 10 Br 7 ] 2+ ( i Pr 2 -bimy = 1,3-diisopropylbenzimidazolin-2-ylidene) (1), was synthesized by direct reduction of AuSMe 2 Cl and i Pr 2 -bimyAuBr with NaBH 4 in one pot. X-rayc rystallization analysis revealed that the cluster comprises two centered Au 13 icosahedra sharing av ertex. Cluster 1 is highly stable and can survive in solution at 80 8 8Cf or 12 h, which is superior to Au 25 nanoclusters passivated with phosphines or thiols.DFT computations reveal the origins of both electronic and thermal stability of 1 and point to the probable catalytic sites.T his work provides new insights into the bonding capability of N-heterocyclic carbene to Au in ac luster,a nd offers an opportunity to probe the catalytic mechanism at the atomic level.

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Indoles — A promising scaffold for drug development

Cited by 532 publications

References 53 publications

Assessments of iodoindoles and abamectin as inducers of methuosis in pinewood nematode, Bursaphelenchus xylophilus

Assessments of iodoindoles and abamectin as inducers of methuosis in pinewood nematode, Bursaphelenchus xylophilus

Transition‐Metal‐Free Synthesis of Heterobiaryls through 1,2‐Migration of Boronate Complex

Highly Robust but Surface-Active: N-Heterocyclic Carbene-Stabilized Au25 Nanocluster as a Homogeneous Catalyst

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