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Home Mesoionic Cpds

Mesoionic Compounds - SYDNONES AND SYDNONE IMINES in AKos Samples.

Download file with mesoionic compounds that were synthesized and were once on stock:
mesoionic-stock.sdf,
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Go to a spreadsheet of ca. 4000 mesoionic compounds or download the spreadsheet as .xls file.

Sydnone and sydnoneimines are mesoionic aromatic heterocyclics, derivatives of 1, 2,3-oxadiazole system. They possess an unique physical and chemical properties, which is result of unusual ring construction. Biological properties of the compounds are of  great interest. The title substructure can be found in the stimulant drugs feprosidnine and mesocarb and the vasodilator molsidomine.
The first review on the chemistry of the compounds: The Chemistry of Sydnone Imines V G Yashunskii and L E Kholodov 1980 Russ. Chem. Rev. 49, 28.

Sydnone, the potential basic pharmacodynamic nucleus has been reported

McNaught A D in, Adv Heterocyclic Chem, Katritzky A R and Boulton A J (Eds.),Advances Heterocyclic Chemistry, Academic Press New York, 1976, 175-319.
 Moustafa M A, Nasr M N, Gineinah M M and Bayoumi W A,
Arch Der Pharmazie,2004, 337, 164-170.
 Kavali R Jyoti and Badami B V,
Farmaco, 2000, 55(5), 406-409.

to a wide variety of biological activities:

Antitumor (anticancer):

Dunkley C S and Thoman C J, Bioorg Med Chem Lett., 2003, 13(17), 2899-2901.
Grynberg N., Gotes R., Miller J., Echevarria A.// Anticancer. Res.-1992.-V.12.- N3.- p.1025-1028; C.A. 1992.-117.-142871t.
Dunkley C.S., Thoman C.J. Synthesis and biological evaluation of a novel phenyl substituted sydnone series as potential antitumor agents.// Bioorg. Med. Chem. Lett.-13.-2003.- p.2899-2901.
Halila G.C. et.al. Effect of sydnone SYD-1, a mesoionic compound On energy-linked function of rat liver mitochondria.// Chemico-Biological interactions.- 169.-  2007.- p. 160-170.
Kier L.B., Roche E.B.// J.Pharm. Sci.- 1965.- V.56.- p.149-167.
Anticancer:

Thamotharan S, Parthasarathi V, Mallur S, Kamble R, Badami B and Linden A, Acta Cryst., 2004, E60, 701-702.

Anti-inflammatory and analgesic: Kalluraya B, Rahiman A M, Polish J Chem., 1997, 71, 1049-1052. Hill J.B., Ray R.E.// J. Med. Chem.- 1975.- V.18.- N1.- p.51-53.
Abdul Rahiman M., Kalluraya B., Hegde J.C. Sydnone derivatives part IX: synthesis, antimicrobial and  pharmacological activity of some sydnone-N-Mannich bases.// Indian journal of Heterocyclic Chem.- v.12.-2003.-p.241-244.
Abdul Rahiman M., Kalluraya B. Sydnone derivatives: part X synthesis and  pharmacological activity of some novel cyclohexenones and indazolinones.// Indian journal of chemistry section B Org. and Med.Chem.- v.42.-2003.-p.1141-1148.
Abdul Rahiman M., Kalluraya B., Banji D. Sydnone derivatives: part V synthesis and  pharmacological properties of some novel triazolothiadiazepin.// Indian journal of chemistry section B Org. and Med.Chem.-v.41.-2002.-p.1712-1717.
Mackie J.E.// Biochim.Pharmacol.- 1990.- V.39.-N11.- p.1767-1774.
Satyanarayana K., Rao M. N. A.// Indian. Drugs.- V.30.- N7.-1993.-p.313-318; C.A., 1994.- 120.- 45418e.
Krishna G., Bharathi V.B., Gurubasav S.P.// Arch. Pharm.- 1980.- V.313.- p.684-688.
Abdul Rahiman M., Kalluraya B., Banji D. Sydnone derivatives. Part VII: synthesis of some novel triazoles and their pharmacological properties.// Arch. Pharm. Pharm. Med.Chem.-2001.-334.-p.263-268.
Antiviral :

Pandey V K and Tandon M, Indian J Heterocycl Chem,, 2006, 15, 399-400.
Bourinbaiar A S, Tan X and Nagorny R,
Acta Virol., 1993, 37, 241-250.

Scavenging activity: Shih M H and Ke F Y, Bioorg Med Chem., 2004, 12, 4633-4633.
Antimalarial: Friedman M D, Stotter P L, Porter T H and Folkers K, J Med Chem., 1973, 16(11), 1314-1316.
Effective endogenous donor NO:

Dendorfer A. // HerZ 1996. D. 21 (Anh. 1). S. 38.
Schonafinger R. // II Farmaco 1999. Vol. 54. P.316.
Newton C.G., Ramsden C. A. // Tetrahedron 1982. Vol. 38. P. 2935.

Aantihypertensive activity, example

 

ethoxycarbonyl-(3-morpholinooxadiazol-3-ium-5-yl)azanide


XLFWDASMENKTKL-UHFFFAOYSA-N


InChI=1S/C9H14N4O4/c1-2-16-9(14)10-8-7-13(11-17-8)12-3-5-15-6-4-12/h7H,2-6H2,1H3

Molsidomine

Antiischemic activity

Bohn H., Deyerle R., Martorana P. A., Schonafinger K.J. // Cardiovasc. Pharmacol., 1991. Vol. 18. P. 522.
Feelisch M. // Naunyn-Schmiedebergs Arch. Pharmacjl., 1998. Vol. 358.
Megson I.L. // Drugs Future 2000, 25. P. 701.
Bohn H., Martorana P. A., Schonafinger K.J. // Eur. J. Pharmacol., 1992. Vol. 220. P. 71.

Antiischemic activity, example

 

[3-[(2S,6R)-2,6-dimethyl-1-piperidyl]oxadiazol-3-ium-5-yl]-(4-methoxybenzoyl)azanide

InChI=1S/C17H22N4O3/c1-12-5-4-6-13(2)21(12)20-11-16(24-19-20)18-17(22)14-7-9-15(23-3)10-8-14/h7-13H,4-6H2,1-3H3/t12-,13+
 

TXPUBJSOHAMNEI-BETUJISGSA-N

Pirsidomin

Antithrombotic activity

Annual Drug Data Rep. / Ed. J. R. Prous. 1991. Vol. 13, №11. P. 945.
Wang George Peng, Xian Ming, Tang Xiaoping et. al. Nitric Oxide Donors: Chemical Activities and Biological Applications. // Chem. Rev. 2002, 102, P. 1091-1134.
Rehse K., Schleifer R., Cuborski T. New NO-donors with antithrombotic and vasodilating activities. II: 3-Alkyl-N-nitroso-5 sydnone imines. // Arch. Pharm. (Weiningem, Ger.) 1993. V. 326, № 10. P. 791-797.
Rehse K., Schleifer K.-J., New NO-donors with antithrombotic and vasodilating activities, III: 3,4-disubstituted N-nitroso-5 sydnone imines. // Arch. Pharm. (Weiningem, Ger.) 1993. V. 326, № 12. P. 929-939.

Rehse K., Schleifer K.-J. et. al., New NO-donors with antithrombotic and vasodilating activities, IV: Chemical Reactivity of Nitrosimines and its Implications for their Pharmacologic Properties. // Arch. Pharm. (Weiningem, Ger.) 1994. V. 327, № 6. P. 359-364.

Aticancer [antitumor]: Kier L.B., Roche E.B. Molecular orbital calculation of the electronic structure of the sydnones. // J. Pharm. Sci. 1965. V. 56, P. 149-167.
Central and peripheral nervous system:

Boenringer Ingelheim, Novel Sydnonimine derivatives, the preparation thereof and compositions containing the same. // Патент ФРГ 1,198,283, 1967; С.А., 1967, 35049.
Pastushenkov B.A., Badyshov B.A. Improvment of human resistanse to high air temperature using drugs. // (Inst. Aviats. Kosm. Med., Moscow Russia). Med. Tr. Prom. Ekol. 1995. V. 9. P
. 39-42.; C.A. 1996, 124, 45664.
Li Shuang, Quock Raymond M. Effects of a nitric oxide donor on behavior and interaction with nitrou oxide in the mouse light/dark exploration test. // European Journal of Pharmacology, 2002, 447,
Р. 75 78.

Central nervous system:

Abdul Rahiman M., Kalluraya B., Banji D. Sydnone derivatives. Part VII: synthesis of some novel triazoles and their pharmacological properties.// Arch. Pharm. Pharm. Med.Chem.-2001.-334.-p.263-268.
Kier L.B.// J.Pharm. Sci.- 1967.- V.56.- p.149.
Bheemarao G.U., Bharjti V., Gurubasav S.P.// Arch. Pharm.- 1978.- V.311.- p.109-114.

Fungicidal activity:

Pilli H., Safak C., Abbasoglu U.// Arch. Pharm (Weinheim, Ger.).- 1993.- V.326.- N9.- p.559-561; C.A., 1994.- 120.- 244853a.
Lingappa B., Kalluraya B., Nooji S.R. Synthesis and  biological study of some novel 4-[5-(4,6-disubstituted-2-thiomethylpyrimidyl)-41-amino-1,2,4-triazol-31-yl]thioacetyl-3-arylsydnones.// Phosphorus. Sulfur, and silicon and the related.

Analgetic anticonvulsive spasmolytic: Tien Hsien Ju, Tsai Yan Hong, Yeh Wen Yuan; Lee Yaw Kuen, Ho Yong Shang// J. Chin. Chem. Soc. (Taipei).- 1990.-V.37.- N1.- p.79-84; C.A., 1990.- 112.- 191419
Antibacterial:

UK 1407540 (1975); C.A., 1977.- 87.- 135343f.
Moustafa A. Mohamed et.al. Novel analogues of sydnone: synthesis, characterization and antibacterial evaluation. // Arch. Pharm. Pharm. Med.Chem.-2004.-337.-p.427-433.
Moustafa A. Mohamed et.al. Synthesis and biological testing of novel analogues as potential antibacterial agents. // Arch. Pharm. Pharm. Med.Chem.-2004.-337.-p.164-170.
Latthe P.R. et.al. Curtius rearrangement reactions of 3-(4-azidocarbonyl)phenylsydnone. Syntesis of 4-(sydnon-3-yl)phenyl carbamates, N-aryl-N1-[4-(sydnon-3-yl)]phenyl ureas and their antimicrobial and insecticidal activities.//J.Chem.Sci.-v.118.-N3.-2006.-p.249-256.

Antioxidant:

Mei-Hsiu Shih, Fang-Ying Ke. Synthesis and evaluation of antioxidant activity of sydnonyl substituted thiazolidinone and thiazoline derivatives.// Bioorg. Med. Chem.-12.-2004.- p.4633-4643.
Mei-Hsiu Shih, Yu-Sheng Su, Cheng-Ling Wu. Synthesis of aromatic substituted hydrazino-thiazole derivatives to clarify structural characterization and antioxidant activity between 3-arylsydnonyl and aryl substituted hydrazino-thiazoles.// Chem.Pharm.Bull.-v.55.-N8.-2007.-p.1126-1135.

 

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