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Chemical compound
Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman[1] and Auguste Laurent[2] in 1840 as a product from the oxidation of indigo dye by nitric acid and chromic acids.
Isatin is a well-known natural product which can be found in plants of the genus Isatis, in Couroupita guianensis,[3][4] and also in humans, as a metabolic derivative of adrenaline.[5]
It looks like a red-orange powder, and it is usually employed as building block for the synthesis of a wide variety of biologically active compounds including antitumorals,[6] antivirals,[7] anti-HIVs,[8] and antituberculars.[9]
The isatin core is also responsible for the color of “Maya blue” and “Maya yellow” dyes.[10]
^Erdmann, Otto Linné (1840). "Untersuchungen über den Indigo". Journal für Praktische Chemie. 19 (1): 321–362. doi:10.1002/prac.18400190161.
^Laurent, Auguste (1840). "Recherches sur l'indigo". Annales de Chimie et de Physique. 3 (3): 393–434.
^Pinto, A. C. (2001). "The chemistry of isatins: a review from 1975 to 1999". J. Braz. Chem. Soc. 12 (3): 273. doi:10.1590/S0103-50532001000300002.
^Bergman, J. (1988). "The structure and properties of some indolic constituents in Couroupita guianensis aubl". Tetrahedron. 41 (14): 2879. doi:10.1016/S0040-4020(01)96609-8.
^Chiyanzu, I. (2003). "Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain". Bioorg. Med. Chem. Lett. 13 (20): 3527–30. doi:10.1016/S0960-894X(03)00756-X. PMID 14505663.
^Mallamo, J.P. (2006). "Structure-guided identification of novel VEGFR-2 kinase inhibitors via solution phase parallel synthesis". Bioorg. Med. Chem. Lett. 16 (8): 2158–62. doi:10.1016/j.bmcl.2006.01.063. PMID 16460933.
^He, Y. (2006). "Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors". Bioorg. Med. Chem. Lett. 16 (8): 2109–12. doi:10.1016/j.bmcl.2006.01.066. PMID 16464578.
^Sriram, D. (2005). "Synthesis and evaluation of anti-HIV activity of isatin beta-thiosemicarbazone derivatives". Bioorg. Med. Chem. Lett. 15 (20): 4451–5. doi:10.1016/j.bmcl.2005.07.046. PMID 16115762.
^Bin-Jubair, F.A.S. (2010). "Anti-Tubercular activity of Isatin and Derivatives". Int. J. Res. Pharm. Sci. 1: 113.
^Vuzquez de Agredos-Pascual, M.L. (2011). "From Maya Blue to "Maya Yellow": A Connection between Ancient Nanostructured Materials from the Voltammetry of Microparticles". Angew. Chem. Int. Ed. 50 (25): 5741–4. doi:10.1002/anie.201100921. PMID 21557419.
Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman and...
and sorbitol. Oxyphenisatin has cathartic properties. The ketone group of isatin (1) is nonenolizable and has interesting properties. In strong acid it becomes...
Another use is as a dissolved ozone indicator through the conversion to isatin-5-sulfonic acid. This reaction has been shown not to be specific to ozone...
(also known as the Pfitzinger-Borsche reaction) is the chemical reaction of isatin with base and a carbonyl compound to yield substituted quinoline-4-carboxylic...
acid, which serves as the desiccant. Notably, it is used to synthesize isatin. In this synthesis, chloral hydrate reacts with aniline and hydroxylamine...
Viktor Meyer in 1882 as a contaminant in benzene. It was observed that isatin (an indole) forms a blue dye if it is mixed with sulfuric acid and crude...
synthesis, using anthranilic acid and ketones Pfitzinger reaction using an isatin with base and a carbonyl compound to yield substituted quinoline-4-carboxylic...
synthesis of indigo. He described his first synthesis of indigo in 1878 (from isatin) and a second synthesis in 1880 (from 2-nitrobenzaldehyde). (It was not...
to develop with the study of the dye indigo. Indigo can be converted to isatin and then to oxindole. Then, in 1866, Adolf von Baeyer reduced oxindole to...
Notably, Smith synthesized their own BCA via the Pfitzinger reaction of isatin and acetoin, substituting NaOH for KOH but otherwise following the synthetic...
been named the Claisen rearrangement. Synthesis of isatin via a process known as the Claisen isatin synthesis, described for the first time in 1879. Designer...
of isatin. and several reactions have been named after him: Sandmeyer isonitrosoacetanilide isatin synthesis(1919) and Sandmeyer diphenylurea isatin synthesis(1903)...
Bisoxatin (formula: C20H15NO4) is a laxative. It can be synthesized from isatin. Reddy, Srinivas Reddy Desi; Rane, Dnyandev Ragho; Velivela, Srinivas Rao;...
Indole-5,6-quinone, a chemical present in the browning reaction of fruits Isatin Phthalimide This set index page lists chemical structure articles associated...
ANGSTROM CRYSTAL STRUCTURE OF CASPASE-3 (APOPAIN OR CPP32)IN COMPLEX WITH AN ISATIN SULFONAMIDE INHIBITOR. 1i3o: CRYSTAL STRUCTURE OF THE COMPLEX OF XIAP-BIR2...
antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin-4(3H)-one". Pharmaceutica...
ordinary bond of this type is only 148 pm and for comparison the C-C bond in isatin is 154 pm long. On the other hand, no change is recorded in the aromatic...
published. Note that nomifensine was a Progenitor to Gastrophenazine. See also: Isatin derivatives. The alkylation between N-methyl-2-nitrobenzylamine [56222-08-3]...
rearrangement, a chemical reaction of an allylic ester with strong base Claisen isatin synthesis 5243 Clasien, a minor planet This disambiguation page lists articles...
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