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Oxyphenisatine

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Oxyphenisatine
Kekulé, skeletal formula of oxyphenisatine
Names
Preferred IUPAC name
3,3-Bis(4-hydroxyphenyl)-1,3-dihydro-2H-indol-2-one
Other names
Dihydroxydiphenylisatin;[1] Diphenolisatin;[1] Oxyphenisatin[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.299 Edit this at Wikidata
EC Number
  • 204-728-1
KEGG
UNII
  • InChI=1S/C20H15NO3/c22-15-9-5-13(6-10-15)20(14-7-11-16(23)12-8-14)17-3-1-2-4-18(17)21-19(20)24/h1-12,22-23H,(H,21,24) checkY
    Key: SJDACOMXKWHBOW-UHFFFAOYSA-N checkY
  • InChI=1/C20H15NO3/c22-15-9-5-13(6-10-15)20(14-7-11-16(23)12-8-14)17-3-1-2-4-18(17)21-19(20)24/h1-12,22-23H,(H,21,24)
    Key: SJDACOMXKWHBOW-UHFFFAOYAU
  • Oc1ccc(cc1)C1(C(=O)Nc2ccccc12)c1ccc(O)cc1
  • OC1=CC=C(C=C1)C1(C(=O)NC2=C1C=CC=C2)C1=CC=C(O)C=C1
Properties
C20H15NO3
Molar mass 317.344 g·mol−1
log P 1.398
Acidity (pKa) 9.423
Basicity (pKb) 4.574
Pharmacology
A06AB01 (WHO)
Oral, rectal
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Oxyphenisatine (or oxyphenisatin) is a laxative.[3] It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long-term use is associated with liver damage,[4] and as a result, it was withdrawn in most countries in the early 1970s. The acetate derivative oxyphenisatine acetate was also once used as a laxative.

Natural chemical compounds similar to oxyphenisatine may be present in prunes,[5] but a recent review of the relevant scientific literature suggests that the laxative effect of prunes is due to other constituents including phenolic compounds (mainly neochlorogenic acids and chlorogenic acids) and sorbitol.[6] Oxyphenisatin has cathartic properties.

Synthesis

[edit]

The ketone group of isatin (1) is nonenolizable and has interesting properties. In strong acid it becomes protonated, and the oxygen can be replaced by electron rich moieties.

Oxyphenisatin synthesis:[7]

In 1885, it was reported that condensation of isatin with phenol 2 leads to oxyphenisatin (3), which can then also be acetylated to (4).

Derivatives

[edit]
  1. Phenisatin (Triacetyldiphenolisatin, Laxagetten, Unilax, Trisatin)
  2. Nicoxyphenisatin
  3. Cinnoxyphenisatin
  4. Cofisatine [54063-34-2]

References

[edit]
  1. ^ a b c SciFinder Scholar, version 2004.2; Chemical Abstracts Service, Registry Number 125-13-3, accessed September 1, 2011
  2. ^ 21 CFR 216.24
  3. ^ Farack, U. M.; Nell, G. (1984). "Mechanism of Action of Diphenolic Laxatives: The Role of Adenylate Cyclase and Mucosal Permeability". Digestion. 30 (3): 191–194. doi:10.1159/000199105. PMID 6548720.
  4. ^ Kotha, P.; Rake, M. O.; Willatt, D. (1980). "Liver Damage Induced by Oxyphenisatin". British Medical Journal. 281 (6254): 1530. doi:10.1136/bmj.281.6254.1530. PMC 1714947. PMID 6893676.
  5. ^ Baum, H. M.; Sanders, R. G.; Straub, G. J. (1951). "The Occurrence of a Diphenyl Isatin in California Prunes". Journal of the American Pharmaceutical Association. 40 (7): 348–349. doi:10.1002/jps.3030400713. PMID 14850362.
  6. ^ Stacewicz-Sapuntzakis, M.; Bowen, P. E.; Hussain, E. A.; Damayanti-Wood, B. I.; Farnsworth, N. R. (2001). "Chemical Composition and Potential Health Effects of Prunes: A Functional Food?". Critical Reviews in Food Science and Nutrition. 41 (4): 251–286. doi:10.1080/20014091091814. PMID 11401245. S2CID 31159565.
  7. ^ Baeyer, A.; Lazarus, M. J. (1885). "Ueber Condensationsproducte des Isatins". Berichte der Deutschen Chemischen Gesellschaft. 18 (2): 2637. doi:10.1002/cber.188501802170.


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