A novel serotonin antagonist 2,2′‐bis[3‐(2‐<i>N,N</i>‐dimethylaminoethyl)indolyl]sulfide (BDIS)

Chu, Chit‐Kay; Wander, Joseph D.; Tackett, Randall L.; Iturrian, W. B.; Jacob, Schmitz,; Garner, Garland E.; Chae, Kun

doi:10.1002/jhet.5570210664

Cited by 3 publications

(2 citation statements)

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“…[17][18][19] In 1974, Hino et al reported the first synthesis of 2,2'-thiobisindole, by the treatment of 3-methyl indole and thiourea with iodine in ethanol. [20] In 1984, Chu et al [21] described the serotonin antagonist properties of 2,2'-bis[3-(2-N,N-dimethylaminoethyl)indolyl]sulfide, and Shirani et al [22] utilized methyl l-methyl-lH-indole-3-acetate and sulphur monochloride to produce the minor product bis(phenylsulfonyl) sulfide and the major product bis(phenylsulfonyl)disulfides. Further, Shirani and Janosik described an alternative method for synthesis of 2,2'thiobisindole (Scheme 1a).…”

Section: Introductionmentioning

confidence: 99%

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Selective Functionalization of Indole: Synthesis of Bioinspired 2,2′‐thiobisindoles, 3‐substituted Oxindoles, and 1‐(chloromethyl) Indoline‐2‐dione in One‐pot manner

Sharma,

Kumar,

Erande

2024

ChemistrySelect

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Indolyl thioethers and indolin‐2‐one motifs are extremely common in pharmaceuticals and organic materials, therefore developing a method to create these scaffolds is considered to be a vital endeavour in the chemical sciences. Here we have reported a unified strategy developed by the fine‐tuning of catalyst‐solvent combination [SOCl2 /AlCl3 in CHCl3 and SOCl2/DMSO (1 : 1) in CHCl3 at 25 °C] towards selective functionalization of Indole to synthesize 2,2′‐thiobisindoles and 3‐chloro‐3‐alkyl substituted oxindoles selectively in one‐pot manner with good to satisfactory yield (52‐86 %; 26 Examples). In application, reactions of 3‐subsituted indole and isatin derivatives produced the 1‐(chloromethyl) indoline‐2,3‐diones by just changing the reaction condition (60 °C), which shows the synthetic utility of the developed method.

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Section: Introductionmentioning

confidence: 99%

“…reported the first synthesis of 2,2′‐thiobisindole, by the treatment of 3‐methyl indole and thiourea with iodine in ethanol [20] . In 1984, Chu et al [21] . described the serotonin antagonist properties of 2,2′‐bis[3‐(2‐ N,N‐ dimethylaminoethyl)indolyl]sulfide, and Shirani et al [22] .…”

Section: Introductionmentioning

confidence: 99%