Indoles isatins

In this chapter, an attempt has been made to present a total of 30 QSAR models on 17 different heterocyclic compound series (acridine, benzimidazole, benzothiazole, camptothecin, flavonoid, indole, isatin, isoquinoUne, oncodazole, paclitaxel, phenanthridine, phenazine, podophyllotoxin, pyrrole, quinocarcin, quinoline, and quinolone) for their cytotoxic activities against various cancer cell lines. The QSARs have been found to be well correlated with a number of physicochemical and structural parameters. The most important parameter for these correlations is hydrophobicity, which is one of the most important determinants for the activity. 

An unidentified rod-shaped gram-negative organism isolated from tap water has been adapted to indole (634). Analysis of simultaneous adaptations indicates that in this organism indole is oxidized by the following steps indole - (indoxyl) - (dihydroi indole) - isatin - formylanthranilic acid - anthranilic acid - salicylic acid... 

Preliminary studies with a thio derivative of isatin (indole-2-thione-3-phenylhydrazone) also showed the hydrazone structure to be the favored tautomeric form (81JOC2764). 

Bei der Reduktion von 2-Oxo-2,3-dihydro-indolen liegen die Ausbeuten iiber 80% d.Th. Das 3-Methyl-Derivat ergibt z. B. quantitativ 3-Methyl-indol (Skatol) Aus den Isatinen erhalt man die entsprechenden Indole in 45-80%iger Ausbeute. Isatin selbst liefert 72% d.Th. Indol. Zur Herstellung von 3,3-Bi-indolen aus den entsprechenden Lactamen s. Lit.4. 

Aus Isatin-3-hydrazon (bzw. 3-Diazo-2-oxo-2,3-dihydro-indol) entsteht in waBriger Pufferlosung 3-Amino-2-oxo-2,3-dihydro-indol4. 

The degradation of indole-3-acetate has been examined in Bradyrhizobium japonicum and was initiated by oxidation to isatin that was hydrolyzed to 2-aminophenylglyoxylate and anthranilic acid (Figure 10.6) (Jensen et al. 1995). 

A more highly oxidized indole relative is isatin (47). The ketonic carbonyl group is nonenolizable and has interesting properties. In strong acid it... 

Yoshikawa M, Murakami T, Kishi A, et al. Novel indole S,0-bisdesmoside, calantho-side, the precursor glycoside of tryptanthrin, indirubin, and isatin, with increasing skin blood flow promoting effects, from two Calanthe species (Orchidaceae). Chem Pharm Bull (Tokyo) 1998 46 886-888. 

The microbial pathways observed for the degradation of indole differ significantly between microorganisms. Four pathways have been reported for indole degradation. In the first pathway, the degradation of indole by Desulfobacterium indolicum was reported [339,340] to occur via isatin and anthranilate (Fig. 25). 

Spiro[3H-indole-3,5(4.H)-(l,2,4)triazoline]-2-one derivatives 204 have been obtained using microwave irradiation in the reaction between imines of isatin 203 and nitrile imines generated in situ from the corresponding hydrazonyl chlorides 199 (Scheme 9.63). The yields are in the range 85-95% and the reaction is complete within 5 min [110]. Similar reactions performed under thermal conditions were complete in 6-10 h and yields decreased to 20-30%. However, when the reaction was performed at ambient temperature, the products were obtained in excellent yields but only after a prolonged reaction time (30 h). 

The imidazo[ 1,2-b][l,2,4]triazino[5,6-6]indoles 597 were prepared by reacting 3-amino[l, 2,4]triazino[5,6-6]indole 592 with a-bromoketones 596. The structure was confirmed by the identity with the product of a reaction between isatin 599 or 2-phenylimino-3-oxoindole 600 and 1,2-diamino-4,5-diphenylimidazole 598 (82ZOR1272). Similarly, a cyclocondensation of 1,2-diamino-4-arylimidazoles with isatin and N-methylisatin was carried out (82KGS242). 

Cyclocondensation of isatin hydrazones 620 with 621 in strong acid gave thiazolo[3, 4 2,3][l,2,4]triazino[5,6-6]indoles 622, which underwent conventional reaction with 2-methyl-3-ethylbenzothiazolium perchlorate 623 to form unsymmetrical cyanines 624 (83URP1054350 85KGS211). The spectral properties of a series of polymethine dyes were examined (88KGS1547). 

Indoles from isatins or oxindoles via diborane Synthesis 2,84 (1972)... 

Cbemical/Physical. The aqueous chlorination of indole by hypochlorite/hypochlorous acid, chlorine dioxide, and chloramines produced oxindole, isatin, and possibly 3-chloroindole (Lin and Carlson, 1984). 

Isatin, see Indole Isatoic acid, see Indole l(3/i) -Isobenzofuranone, see Naphthalene Isobutylbenzene, see Butylbenzene, PCB-1242... 

Oximes and their derivatives are widely used in organic synthesis. A number of reviews are devoted to the chemistry and biological activity of oximes and their derivatives The synthesis, reactions and biological activity of oximes containing a heterocyclic substituent, e.g. furan and thiophene", indole and isatin, pyridine, pyrrole, quinoline and five-membered heterocycles with two heteroatoms have been reviewed. 

The antitumor activities of indole and isatin oximes and of furan oximes were studied by several investigators. Furan oximes were found to inhibit DNA, RNA and protein synthesis in lipoid leukemia cells. Derivatives of quinoline oximes were also shown to possess antitumor activity , and glucosinolates, 15, were suggested as cancer-preventive agents . ... 

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