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| Submission declined on 2 December 2024 by Ibjaja055 (talk). Contains grammatical errors and unclear sentences like:
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| Submission declined on 1 December 2024 by Graeme Bartlett (talk). Contains a lot of unclear text in incomplete sentences. Please rewrite everything past the first 2 sentences with complete standalone sentences that can be read without consulting references. eg describe the synthesis. Declined by Graeme Bartlett 2 days ago. | |
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| Clinical data | |
|---|---|
| Other names | gastrofenzin, AN5, DZO-200. |
| Identifiers | |
| CAS Number |
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| PubChem CID | |
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| ChEMBL | |
| Chemical and physical data | |
| Formula | C19H21ClN2O2 |
| Molar mass | 344.84 g·mol−1 |
| 3D model (JSmol) | |
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Gastrophenzine is a Bulgarian antiulcerogenic drug. It is related to Nomifensine. AN5 possesses an antiulcer activity many times higher than that of ranitidine and cimetidine.[1]
A study found that gastrophenzine lacked genotoxicity and was non-mutagenic.[2]
By virtue of its dopaminergic properties, AN5 might also be indicated off-label for use in the treatment of either depression or Parkinson’s Disease.
Compare also for other aniline containing urethane drugs: Bonnecor, Ethacizine and Moricizine.
Synthesis
edit
The alkylation of N-Methyl-2-Nitrobenzylamine [56222-08-3] (1) with 4-Chlorostyrene oxide [2788-86-5] (2) affords N-(2-nitrobenzyl)-2-(methylamino)-1-(4-chlorphenyl)-1-ethanol (3). The reduction of the nitro group with NaBH4/NiCl2 in boiling methanol gave N-(2-aminobenzyl)-2-(methylamino)-1-(4-chlorphenyl)-1-ethanol [102436-79-3] (4). Urethane formation with ethyl chloroformate results in N-[2-(ethoxycarbonyl)amino]-2-(methylamino)-1-(4-chlorophenyl)-1-ethanol (5). The latter is cyclodehydrated by means of conc.H2SO4 in dichloroethane to Gastrophenazine (6).
According to method B, the amino alcohol (4) is cyclodehydrated by conc. H2SO4 to 8-amino-4-(4-chlorophenyl)-2-methyl-1,2,3-4-tetrahydroisoquinoline, PC14493695 (7). Urethane formation with ethyl chloroformate also gives Gastrophenazine.
References
edit- ^ Ivanova N, Mondeshka D, Ivanov C, Angelova I, Terziyska S, Paskov V (1990). "A new class of antiulcer drugs. I. Antiulcer effect of AN5, a 4-phenyl-tetrahydroisoquinoline derivative, on different experimental models of ulcer in rats". Methods and Findings in Experimental and Clinical Pharmacology. 12 (6): 401–10. PMID 2087139.
- ^ Mirkova E (1994). "[The genotoxicity and carcinogenic potential of gastrofenzin]". Eksperimentalna Meditsina I Morfologiia (in Bulgarian). 32 (3–4): 57–68. PMID 8857033.
- ^ Ivanova N, Angelova J, Mondeshka D, Ivanov C (1992). "Gastrophenzine: Antiulcer". Drugs of the Future. 17 (2): 104. doi:10.1358/dof.1992.017.02.164146.
- ^ Ivanova N, Ivanov T, Mondeshka D, Berova N, Angelova I, Rakovska R, et al. (January 1990). "[Synthesis, stereochemistry and anticonvulsant action of 4-phenyltetrahydroisoquinolines]". Archiv der Pharmazie (in German). 323 (1): 3–7. doi:10.1002/ardp.19903230103. PMID 2334267.
- ^ US 4537895, Deak G, Zara E, Gyorgy L, Fekete M, Doda M, Seregi A, Kanyicska B, Toth E, Horvath M, Manyai S, Gorgenyi F, Vaszovics G, "Isoquinoline derivatives", issued 27 August 1985, assigned to Egyt Gyogyszervegyeszeti Gyar
- ^ Zára-Kaczián E, György L, Deák G, Seregi A, Dóda M (July 1986). "Synthesis and pharmacological evaluation of some new tetrahydroisoquinoline derivatives inhibiting dopamine uptake and/or possessing a dopaminomimetic property". Journal of Medicinal Chemistry. 29 (7): 1189–95. doi:10.1021/jm00157a012. PMID 3806569.