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Sulfoxides

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Definition: Organic compounds that have the general formula R-SO-R. They are obtained by oxidation of mercaptans (analogous to the ketones). (From Hackh's Chemical Dictionary, 4th ed)     
Examples 2-Pyridinylmethylsulfinylbenzimidazoles; Dimethyl Sulfoxide
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
ethyl-6-bromo-5-hydroxy-4-(imidazol-1-yl)-methyl-1-methyl-2-(phenylsulfinylmethyl)-1H-indole-3-carboxylate  0   *Indoles *Sulfoxides. Biomed Chromatogr. 2012 Apr;26(4):458-63.
N-acetyl-S-(2-carbamoylethyl)cysteine-sulfoxide  0   *Sulfoxides Acetylcysteine/*analogs & derivatives. Arch Toxicol 2011 Jun;85(6):601-6
S-methyl-N,N-diethyldithiocarbamoyl sulfoxide  0   *Sulfoxides. Biochimie. 2011 Feb;93(2):286-95
molinate sulfoxide  0   *Sulfoxides *Thiocarbamates. Regul Toxicol Pharmacol 2009 Apr;53(3):195-204
1-(2,4-difluorophenethyl)-4-(4-fluorophenylsulfinyl)piperidine  0   *Piperidines *Sulfoxides Fluorine Radioisotopes Receptor, Serotonin, 5-HT2A. Nucl Med Biol 2010 Jul;37(5):605-14
onionin A  0   *Sulfoxides *Thiophenes. J Nat Prod. 2010 Jul 23;73(7):1306-8
2-(4-(2,2-dimethyl-1,3-dioxan-5-yl)methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl-1H-benzimidazole  0   *Benzimidazoles *Sulfoxides. J Pharmacol Exp Ther 2010 Aug;334(2):395-401
cis-2-methylcyclopentyl phenyl sulfoxide  0   *Cyclopentanes *Sulfoxides. J Org Chem. 2009 Feb 20;74(4):1541-8
sulphoraphane nitrile  0   *Nitriles *Sulfoxides. Phytochemistry 2008 Nov;69(16):2765-73
4-nitrophenyl methyl sulfoxide  0   *Sulfoxides. Org Biomol Chem 2008 Feb 21;6(4):762-71
isoamyl benzothiazolyl sulfoxide  0   *Sulfoxides *Benzothiazoles. Molecules 2005;10(8):912-21
N-methyl-3-(tert-butyl)sulfinyl-1,4-dihydropyridine  0   *Dihydropyridines *Sulfoxides. Molecules 2007;12(3):415-22
6-phenyl-1-(4-tolylsulfinyl)hexa-3,5-dien-2-ol  0   *Hexanols *Sulfoxides. Acta Crystallogr C 2006 Oct;62(Pt 10):o631-2
fenoxon sulfoxide  0   *Sulfoxides Fenthion/*analogs & derivatives. Chem Res Toxicol. 2007 Feb;20(2):257-62
8-phenyl-1,6-octadienyl tolyl sulfide S-oxide  0   *Sulfoxides. Chem Commun (Camb) 2005 Aug 21;(31):3992-4
1,1-dimethyl-2-phenylethyl phenyl sulfoxide  0   *Benzene Derivatives *Sulfoxides. Org Biomol Chem. 2005 May 21;3(10):1977-81
gamma-L-glutamyl-trans-S-1-propenyl-L-cysteine sulfoxide  0   *Dipeptides *Sulfoxides. J Agric Food Chem. 2005 May 4;53(9):3408-14
S(R)-podolactone D  0   *Diterpenes *Lactones *Sulfoxides. J Nat Prod 2003 Feb;66(2):282-4
pebulate sulfoxide  0   *Sulfoxides *Thiocarbamates. J Exp Bot 2003 Apr;54(385):1289-94
1-propenylcysteine sulfoxide  0   *Sulfoxides Cysteine/*analogs & derivatives. Nature 2002 Oct 17;419(6908):685
N-(2-(3,4-dichlorophenyl)-4-(4-(2-methylsulfinylphenyl)-1-piperdinyl)butyl)-N-methyl-2-methoxy-3-cyano-1-naphthamide  0   *Piperidines *Sulfoxides. J Med Chem 2002 Aug 29;45(18):3972-83
N-(2-(3,4-dichlorophenyl)-4-(4-(4-methoxy-2-methylsulfinylphenyl)-1-piperidinyl)butyl)-N-methyl-3-cyano-1-naphthamide  0   *Piperidines *Sulfoxides. J Med Chem 2002 Aug 29;45(18):3972-83
S-n-butylcysteine sulfoxide  0   *Sulfoxides Cysteine/*analogs & derivatives. J Nat Prod 2002 Jul;65(7):960-4
Ro 106-9920  0   *Sulfoxides *Tetrazoles. J Biol Chem 2002 Jun 28;277(26):23573-81
5-(4-fluorophenyl)-2-(2-methanesulfinylbenzylsulfanyl)-4-pyridin-4-ylpyrimidine  0   *Pyrimidines *Sulfoxides. J Med Chem 2002 Jun 20;45(13):2733-40
monochloro(dimethylsulfoxide)(metforminuro) platine(II)  0   *Organoplatinum Compounds *Sulfoxides. Ann Pharm Fr 2002 Mar;60(2):93-101
diethyl sulfoxide  0   *Sulfoxides. Biofizika 2002 Mar-Apr;47(2):315-7
ZD 7944  0   *Piperidines *Sulfoxides Receptors, Neurokinin-2/antagonists & inhibitors. Bioorg Med Chem Lett 2001 Oct 22;11(20):2769-73
S-(4'-histidyl)cysteine sulfoxide  0   *Dipeptides *Sulfoxides. Eur J Biochem 2001 Oct;268(20):5229-41
ZD 6021  0   *Piperidines *Sulfoxides Receptors, Tachykinin/antagonists & inhibitors. J Pharmacol Exp Ther 2001 Jul;298(1):307-15
2-((4-methylthiopyridin-2-yl)methylsulfinyl)benzimidazole  0   *Benzimidazoles *Sulfoxides Protein Tyrosine Phosphatases/antagonists & inhibitors. Bioorg Med Chem Lett 2000 Dec 4;10(23):2657-60
methyl phenyl sulfoxide  1193-82-4   *Sulfoxides. J Biol Chem 2000 Nov 10;275(45):34858-66
ethylmethyl sulfoxide  0   *Sulfoxides. Xenobiotica 1999 Nov;29(11):1101-13
pyrisulfoxin B  0   *Pyridines *Sulfoxides. J Antibiot (Tokyo) 1999 May;52(5):505-7
pyrisulfoxin A  0   *Pyridines *Sulfoxides. J Antibiot (Tokyo) 1999 May;52(5):505-7
2-imino-3-(2-methylsulfinylethyl)-6-trifluoromethoxy-2-benzothiazoline  0   *Sulfoxides *Benzothiazoles. J Med Chem 1999 Jul 29;42(15):2828-43
IY 81149  0   *Benzimidazoles *Sulfoxides H(+)-K(+)-Exchanging ATPase/antagonists & inhibitors. Arch Pharm Res 1999 Apr;22(2):189-93
iso-10-devinylajoene  0   *Disulfides *Sulfoxides. Biosci Biotechnol Biochem 1999 Mar;63(3):588-90
SB 222657  0   *Azetidines *Sulfoxides Phospholipases A/antagonists & inhibitors. Biochem J 1999 Mar 1;338( Pt 2):479-87
N-acetyl-S--(1,2,3,4,4-pentachlorobutadienyl)cysteine sulfoxide  0   *Sulfoxides Cysteine/*analogs & derivatives. Chem Res Toxicol 1998 Jul;11(7):750-7
lincomycin sulfoxide  0   *Sulfoxides Lincomycin/*analogs & derivatives. J Antibiot (Tokyo) 1997 Oct;50(10):866-73
3-(difluoromethyl)-1-(4-methoxyphenyl)-5-(4-(methylsulfinyl)phenyl)pyrazole  151506-44-4   *Pyrazoles *Sulfoxides. Chem Pharm Bull (Tokyo) 1997 Sep;45(9):1475-81
methyl 2-(octylsulfinyl)benzoate  0   *Benzoates *Sulfoxides. Biomed Chromatogr 1997 Sep-Oct;11(5):289-95
3-chloro-N-((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)-4-(phenylsulfinyl)-N-(prop-2-ynyl)aniline  0   *Quinazolines *Sulfoxides Thymidylate Synthase/antagonists & inhibitors. J Med Chem 1997 Feb 28;40(5):677-83
tetranorbiotin sulfoxide  0   *Sulfoxides Biotin/*analogs & derivatives. Am J Clin Nutr 1997 Feb;65(2):508-11
3-(1,2-di-O-palmitoylglycero)sulfinylandrost-5-en-17-one  0   *Sulfoxides Dehydroepiandrosterone/*analogs & derivatives. Steroids 1995 Apr;60(4):321-3
triclabendazole sulfoxide  100648-13-3   *Benzimidazoles *Sulfoxides. Parasitol Res 1993;79(7):529-36
3-(4-methylsulfinylstyryl)-1,2,4-oxadiazole  24664-13-9   *Oxadiazoles *Sulfoxides. J Antimicrob Chemother 1993 Jul;32(1):109-115
S-(4-bromophenyl)cysteine sulfoxide  152406-99-0   *Sulfoxides Cysteine/*analogs & derivatives. Biochem Pharmacol 1993 Oct 5;46(7):1113-7
tillam sulfoxide  51892-60-5 Formamide, N-butyl-N-ethyl-1-(propylsulfinyl)  *Sulfoxides *Thiocarbamates. Biochem Soc Trans 1993 May;21(2):184S
5-chloro-3-(phenylsulfonyl)indole-2-carboxamide  0   *Indoles *Sulfoxides. J Med Chem 1993 Apr 30;36(9):1291-4
2,3,4,6-tetra-O-benzylgalactopyranosyl phenyl sulfoxide  117307-18-3   *Sulfoxides Galactose/*analogs & derivatives. Carbohydr Res 1992 Sep 2;233:245-50
dipropyl sulfoxide  4253-91-2   *Sulfoxides. Biochem Soc Trans 1992 May;20(2):2115
pentachlorophenylmethyl sulfoxide  70215-07-5   *Chlorobenzenes *Sulfoxides. Xenobiotica 1992 Mar;22(3):325-34
4-(methylsulfinyl)phenyl nitrogen mustard  141612-08-0   *Sulfoxides Mechlorethamine/*analogs & derivatives. J Med Chem 1992 May 29;35(11):2137-9
G 4120  143120-27-8   *Peptides, Cyclic *Sulfoxides. J Med Chem 1992 May 29;35(11):2040-8
rufloxacin sulfoxide  132843-25-5   *Sulfoxides *Thiazines *Quinolones. J Chromatogr 1992 Jan 3;573(1):168-72
1,1'-sulfonylbis(2-(methylsulfinyl)ethane)  137371-96-1   *Sulfones *Sulfoxides. J Chromatogr 1991 Oct 11;558(2):405-14
1-methylsulfinyl-2-(2-(methylthio)ethylsulfonyl)ethane  137371-97-2   *Sulfides *Sulfones *Sulfoxides. J Chromatogr 1991 Oct 11;558(2):405-14
2,2'-sulfinylbisethanol  2580-77-0   *Sulfoxides. J Chromatogr 1991 Oct 11;558(2):393-404
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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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