XCII.—Indican. Part III

Thomas, Frederick; Bloxam, William Popplewell; Perkin, Arthur George

doi:10.1039/ct9099500824

Cited by 6 publications

(3 citation statements)

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“…1680 (Meyer & Bellmann, 1886), oxindole, m.p. 1260 (Di Carlo, 1944), indirubin (sublimes at 2440) (Forrer, 1884), indigotin (Thomas, Bloxam & Perkin, 1909) and isatan (Hansen, 1924) were synthesized and purified. Indole, m.p.…”

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confidence: 99%

The metabolism of [2-14C]indole in the rat

King¹,

Parke²,

Rd³

1966

Biochemical Journal

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1. [2-(14)C]Indole has been synthesized from [(14)C]formate and o-toluidine via N[(14)C]-formyltoluidine. 2. When fed to rats, the (14)C of [(14)C]indole (dose 70-80mg./kg. body wt.) is fairly rapidly excreted, and in 2 days an average of 81% appears in the urine, 11% in the faeces and 2.4% as carbon dioxide in the expired air. 3. Radioactivity is excreted in the urine as indoxyl sulphate (50% of the dose), indoxyl glucuronide (11%), oxindole (1.4%), isatin (5.8%), 5-hydroxyoxindole conjugates (3.1%), N-formylanthranilic acid (0.5%) and unchanged indole (0.07%). The faeces contain indoxyl sulphate (0.4% of the dose) and indole (0.2%), but the major metabolites have not been identified. 4. Fed to rats with biliary cannulae an average of 5.6% of a dose of [(14)C]indole (20-60mg./kg. body wt.) is excreted in the bile in 2 days. Radioactivity is present as indoxyl sulphate (0.8% dose) and 5-hydroxyoxindole conjugates (0.6%). 5. Rats further metabolize indoxyl into N-formylanthranilic acid and anthranilic acid, and oxindole into 5-hydroxyoxindole. 6. With rat-liver microsomes plus supernatant under aerobic conditions, indole gives indoxyl, oxindole, possibly isatin, N-formylanthranilic acid and anthranilic acid, but under anaerobic conditions gives only oxindole. Similarly, under aerobic conditions, oxindole gives 5-hydroxyoxindole, anthranilic acid and o-aminophenylacetic acid. 7. Indole is metabolized by two pathways, one via indoxyl to isatin, N-formylanthranilic acid and anthranilic acid, and the other via oxindole to 5-hydroxyoxindole and possibly to o-aminophenylacetic and anthranilic acid. 8. The following new compounds are described: 4-hydroxy-2-nitrophenylacetic acid, 3-, 4- and 5-benzyloxy-2-nitrophenylacetic acid, 5- and 7-hydroxyoxindole and 5-aminoacridine indoxyl sulphate.

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confidence: 99%

The metabolism of [2-14C]indole in the rat

King¹,

Parke²,

Rd³

1966

Biochemical Journal

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“…The biomimetic synthesis developed by Baeyer from indoxyl (26) indisputably has represented a major breakthrough and has been used by several researchers after its discovery (136,(146)(147)(148). However, the ability of indoxyl (26) to dimerize to yield indigotin (8) has led to the necessity of developing a more stable intermediate.…”

Section: Indoxyl Pathwaymentioning

confidence: 98%

“…The lead compound in this series is Natura ® (146). This N-glycosylisoindigo has been synthesized by Wang et al in 2003 (200) from an acetyl-protected isatin N-glycoside.…”

Section: Glycosylisoindigomentioning

confidence: 99%