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| Submission declined on 2 December 2024 by Ibjaja055 (talk). Contains grammatical errors and unclear sentences like: Declined by Ibjaja055 8 days ago.A conclusion of the lack of mutagenicity and of carcinogenic potency of was made | |
| 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 9 days ago. | |
Comment: The synthesis section of this article is very difficult to understand as it is written right now. Please fix its prose to make it more understandable to laypeople (or at least, those only with basic knowledge of biomolecules). I noticed that this is a recurring problem with your articles like Draft:Perithiaden and Draft:TC-C 14G. You may take a look at how to write synthesis sections from places like Methamphetamine#Chemistry Also, the majority of citations are devoted to the Synthesis section. More citations should be about its biological activity. Pygos (talk) 05:56, 7 December 2024 (UTC)
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| Other names | gastrofenzin, AN5, DZO-200. |
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| Formula | C19H21ClN2O2 |
| Molar mass | 344.84 g·mol−1 |
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Gastrophenzine (AN5, DZO-200) 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 to other aniline containing urethane drugs: Bonnecor, Ethacizine and Moricizine.
Synthesis
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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.