Azaprocin

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Azaprocin
180px
Systematic (IUPAC) name
1-(3-((E)-3-phenylprop-2-enyl)- 3,8-diazabicyclo [3.2.1]octan-8-yl) propan-1-one
Legal status
Legal status
  • Legal
Identifiers
CAS Number 448-34-0
ATC code none
PubChem CID 6433185
ChemSpider 16736583
Chemical data
Formula C18H24N2O
Molar mass 284.396[[Script error: No such module "String".]]
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Physical data
Melting point 170 to 175 °C (338 to 347 °F)
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Azaprocin is a drug which is an opioid analgesic with approximately 10x the potency of morphine, and a fast onset and short duration of action.[1][2][3] It was discovered in 1963, but has never been marketed.

The derivative substituted on the phenyl ring with a p-nitro group is more potent than the parent compound, around 25x the potency of morphine.[4] The ring-opened 2,6-dimethylpiperazine analogues are also active,[5] and a large family of opioid analgesic compounds derived from this parent structure have been developed over the last 40 years.[6][7][8][9][10][11][12][13][14][15]

References

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  1. ↑ Cignarella G, Occelli E, Cristiani G, Paduano L, Testa E. Bicyclic Homologs of Piperazine. VI. Synthesis and Analgesic Activity of 3-Substituted 8-Propionyl-3,8-diazabicyclo[3.2.1]octanes. Journal of Medicinal Chemistry 1963; 6(6):764-766. PMID 14184943
  2. ↑ Cignarella G, Occelli E, Testa E. Bicyclic Homologs of Piperazine. VII. Synthesis and Analgesic Activity of 3-Aralkenyl-8-Propionyl-3,8-diazabicyclo[3.2.1]octanes. Journal of Medicinal Chemistry 1965 May;8:326-31. PMID 14323140
  3. ↑ Rosselli del Turco B, Maffii G. Effect of analgesic drugs on the conditioned behavior of rats. (Italian) Bollettino Chimico Farmaceutico. 1968 Feb;107(2):120-6. PMID 5730115
  4. ↑ Cignarella G, Barlocco D, Tranquillini ME, Volterra A, Brunello N, Racagni G. Interaction of 3,8-diazabicyclo (3.2.1) octanes with mu and delta opioid receptors. Pharmacological research communications. 1988, 20(5):383-394. PMID 2843931
  5. ↑ Cignarella G, Testa E. 2,6-Dialkylpiperazines. IV. 1-Propionyl-4-substituted cis-2,6-dimethylpiperazines structurally related to the analgetic 8-acyl-3,8-diazabicyclo[3.2.1]octanes. Journal of Medicinal Chemistry. 1968 May;11(3):592-4. PMID 5656502
  6. ↑ Cignarella G, Barlocco D, Tranquillini ME, Volterra A, Brunello N, Racagni G. Interaction of 3,8-diazabicyclo (3.2.1) octanes with mu and delta opioid receptors. Pharmacology Research Communications. 1988 May;20(5):383-94. PMID 2843931
  7. ↑ Barlocco D, Cignarella G, Greco G, Novellino E. Computer-aided structure-affinity relationships in a set of piperazine and 3,8-diazabicyclo[3.2.1]octane derivatives binding to the mu-opioid receptor. Journal of Computer Aided Molecular Design. 1993 Oct;7(5):557-71. PMID 8294946
  8. ↑ Fadda P, Barlocco D, Tronci S, Cignarella G, Fratta W. Antinociceptive action of DBO 17 and DBO 11 in mice: two 3,8 diazabicyclo (3.2.1.) octane derivates with selective mu opioid receptor affinity. Naunyn Schmiedeberg's Archives of Pharmacology. 1997 Nov;356(5):596-602. PMID 9402039
  9. ↑ Barlocco D, Cignarella G, Vianello P, Villa S, Pinna GA, Fadda P, Fratta W. Synthesis and mu-opioid receptor affinity of a new series of nitro substituted 3,8-diazabicyclo[3.2.1]octane derivatives. Farmaco. 1998 Aug-Sep;53(8-9):557-62. PMID 10081818
  10. ↑ Cignarella G, Barlocco D, Vianello P, Villa S, Pinna GA, Fadda P, Fratta W, Toma L, Gessi S. Benzocondensed derivatives as rigid analogues of the mu-opioid agonist 3(8)-cinnamyl-8(3)-propionyl-3,8-diazabicyclo[3.2.1]octanes: synthesis, modeling, and affinity. Farmaco. 1998 Oct-Nov;53(10-11):667-74. PMID 10205853
  11. ↑ Vianello P, Albinati A, Pinna GA, Lavecchia A, Marinelli L, Borea PA, Gessi S, Fadda P, Tronci S, Cignarella G. Synthesis, molecular modeling, and opioid receptor affinity of 9, 10-diazatricyclo[4.2.1.1(2,5)]decanes and 2,7-diazatricyclo[4.4.0. 0(3,8)]decanes structurally related to 3,8-diazabicyclo[3.2. 1]octanes. Journal of Medicinal Chemistry. 2000 Jun 1;43(11):2115-23. PMID 10841790
  12. ↑ Pinna GA, Murineddu G, Curzu MM, Villa S, Vianello P, Borea PA, Gessi S, Toma L, Colombo D, Cignarella G. Synthesis, modelling, and mu-opioid receptor affinity of N-3(9)-arylpropenyl-N-9(3)-propionyl-3,9-diazabicycl. Farmaco. 2000 Aug;55(8):553-62. PMID 11132733
  13. ↑ Pinna GA, Cignarella G, Loriga G, Murineddu G, Mussinu JM, Ruiu S, Fadda P, Fratta W. N-3(9)-arylpropenyl-N-9(3)-propionyl-3,9-diazabicyclo[3.3.1]nonanes as mu-opioid receptor agonists. Effects on mu-affinity of arylalkenyl chain modifications. Bioorganic and Medicinal Chemistry. 2002 Jun;10(6):1929-37. PMID 11937351
  14. ↑ Pinna GA, Cignarella G, Ruiu S, Loriga G, Murineddu G, Villa S, Grella GE, Cossu G, Fratta W. Synthesis of novel diazatricyclodecanes (DTDs). Effects of structural variation at the C3' allyl end and at the phenyl ring of the cinnamyl chain on mu-receptor affinity and opioid antinociception. Bioorganic and Medicinal Chemistry. 2003 Sep 1;11(18):4015-26. PMID 12927864
  15. ↑ Loriga G, Manca I, Murineddu G, Chelucci G, Villa S, Gessi S, Toma L, Cignarella G, Pinna GA. Synthesis of 3,6-diazabicyclo[3.1.1]heptanes as novel ligands for the opioid receptors. Bioorganic and Medicinal Chemistry. 2006 Feb 1;14(3):676-91. PMID 16243530
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