Structure And Activity Of Aromatic Propenamine Derivatives

This review reports aspects related to the structure and biological activities of compounds possessing the aminoallyl group in their structures (propenamines). The compounds were classified depending on the pharmacological effect as antihistaminic agents, inhibitors of 5-hydroxytriptamine (5-HT) and noradrenaline (NE) uptake, antitripanosomatid, antimycobacterial or as antifungic activity. Cytotoxicity on mammalian cells is also described as well as the importance of some geometric isomers on the biological effect.45378Abe, I., Tomesch, J.C., Wattamasin, S., Prestmich, G.D., Inhibitors of squalene biosynthesis and metabolism (1994) Nat Prod Report, 11, pp. 279-302Adamson, D.W., Barrett, P.A., Billinghurst, J.W., Green, A.F., Jones, T.S.G., Geometrical isomers in a series of antihistamines (1951) Nature, 168, pp. 204-205Adamson, D.W., Barrett, P.A., Billinghurst, J.W., Jones, T.S.G., Aminoalkyl tertiary carbinols and derived products. 6. The stereochemistry of some 1-phenyl-1-2′-pyridylprop-1-enes, and of some 3-(tertiary amino)-1-phenyl-1-2′-pyridylprop-1-enes carrying additional substituents (1958) J Chem Soc, pp. 312-324Adamson, D.W., Barrett, P.A., Billinghurst, J.W., Jones, T.S.G., Minoalkyl tertiary carbinols and derived products. 5. Antihistamines - The stereochemistry of cis-3 and trans-3-phenyl-3-pyridylallylamines (1957) J Chem Soc, pp. 2315-2326Alvi, K.H., Iqbal, N., Khan, K.A., Haroon, T.S., Hussain, I., Aman, S., A randomized double-blind trial of the efficacy and tolerability of terbinafine once daily compared to griseofulvin once daily in treatment of tinea capitis (1992) Royal Society of Medicine Services International Congress Series, No. 205, pp. 35-40. , Shuster S, Jafary MH (eds.). London: Royal Society of Medicine Press LtdAmaral, V.C.S., Dos Santos, S.C., Lima, D.M., Nunes G.P., Jr., Terapias antifúngicas na gestação: Riscos e perspectivas (2001) Infarma (Brazil), 13, pp. 87-91Araujo, C.A.C., Alegrio, L.V., Leon, L.L., Antileishmanial activity of compounds extracted and characterized from Centrolobium sclerophyllum (1998) Phytochem, 49, pp. 751-754Artuc, M., Hermes, B., Steckelings, U.M., Grutzkau, A., Henz, B.M., Mast cells and their mediators in cutaneous wound healing active participants or innocent bystanders? (1999) Exp Dermatol, 8, pp. 1-16Bäckvall, J.E., Nordberg, R.E., Nystrom, J.E., Hogberg, T., Ulff, B., Synthesis of 3-aryl-3-pyridylallylamines related to zimelidine via palladium-catalyzed amination (1981) J Org Chem, 46, pp. 3479-3483Barbe, J., Andrews, P.R., Lloyd, E.J., Brouant, P., Soyfer, J.C., Galy, J.P., Galy, A.M., Individualization of structural patterns of sedative and anti-H-1 actions (1983) Eur J Med Chem, 18, pp. 531-534Barlow, R.B., Franks, F.M., Pearson, J.D.M., Relation between biological-activity and degree of resolution of optical isomers (1972) J Pharm Pharmacol, 24, pp. 753-761Barret, P.A., Beveridge, E., Bull, D., Caldwell, I.C., Islip, P.J., Neal, R.A., Woods, N.C., The efficacy of a novel compound, (E)-1-(4′ bromo-4-biphenylyl)-1-(4-chlorophenyl)-3-dimethylaminoprop-1-ene against Trypanosoma cruzi in mice (1982) Experientia, 38, pp. 338-339Berney, D., Schuh, K., Heterocyclic spiro-naphthalenones. 1. Synthesis and reactions of some spiro[(1h-naphthalenone)-1,3′-piperidines] (1978) Helv Chim Acta, 61, pp. 1262-1273Borea, P.A., Bertolase, V., Gilli, G., Crystallographic and conformational studies on histamine H-1-receptor antagonists. 4. On the stereochemical vector of antihistaminic activity (1986) Arzneimittel-Forschung/Drug Res, 36, pp. 895-899Brandes, L.J., Bogdanovic, R.P., Tong, J.G., Davie, J.R., Labella, F.S., Intracellular histamine and liver-regeneration-high-affinity binding of histamine to chromatin, low affinity binding to matrix, and depletion of a nuclear-storage pool following partial-hepatectomy (1992) Biophys Res Commun, 184, pp. 840-847Brandes, L.J., Queen, G.M., LaBella, F.S., N,N-diethyl-2-[4(phenylmethyl)phenoxy] ethanamine (DPPE), a chemopotentiating and cytoprotective agent in clinical trials: Interaction with histamine at cytochrome P450 3A4 and other isozymes that metabolize antineoplastic drugs (2000) Cancer Chemoth Pharm, 45, pp. 298-304Castellano, S., La Colla, P., Musiu, C., Stefancich, G., Azole antifungal agents related to naftifine and butenafine (2000) Arch Pharm, 333, pp. 162-166Casy, A.F., Drake, A.F., Ganellin, C.R., Mercer, A.D., Upton, C., Stereochemical studies of chiral H-1 antagonists of histamine - The resolution, chiral analysis, and biological evaluation of 4 antipodal pairs (1992) Chirality, 4, pp. 356-366Casy, A.F., Ganellin, C.R., Mercer, A.D., Upton, C., Analogues of tripolidine: Structural influences upon antihistamine activity (1992) J Pharm Pharmacol, 44, pp. 791-795Casy, A.F., Ison, R.R., Stereochemical influences upon antihistamine activity - Further studies of isomeric 4-amino-1,2-diarylbutenes (1970) J Pharm Pharmacol, 22, pp. 270-278Casy, A.F., Antihistamine drugs (1989) Handbook of Stereoisomers: Therapeutic Drugs, pp. 149-164. , Smith DF (ed.). Boca Raton: CRC PressCohen, A.F., Hamilton, M.J., Liao, S.H., Findlay, J.W., Peck, A.W., Pharmacodynamic and pharmacokinetics of BW825C: A new antihistamine (1985) Eur J Clin Pharmacol, 28, pp. 197-204Cohen, A.F., Hamilton, M.J., Philipson, R., Peck, A.W., The acute effects of acrivastine (7) (BW825C), a new antihistamine, compared with triprolidine on measures of central nervous system performance and subjective effects (1985) Clin Pharmacol Ther, 38, pp. 381-386Coppen, A., The biochemistry of affective disorders (1967) Br J Psychiatr, 113, pp. 1237-1264De Conti, R., Gimenez, S.M.N., Haun, M., Pilli, R.A., De Castro, S.L., Durán, N., Synthesis and biological activities of N,N-dimethyl-2-propen-1-amine derivatives (1996) Eur J Med Chem, 31, pp. 915-918De Conti, R., Oliveira, D.A., Fernandes, A.M.A.P., Melo, P.S., Rodriguez, J.A., Haun, M., De Castro, S.L., Durán, N., Application of a multi-endpoint cytotoxicity assay to the trypanocidal compounds 2-propen-1-amine derivatives and determination of their acute toxicity (1998) In Vitro Mol Toxicol, 11, pp. 153-160De Conti, R., Santa Rita, R.M., De Souza, E.M., Melo, P.S., Haun, M., De Castro, S.L., Durán, N., In vitro trypanocidal activities of a novel series of N,N-dimethyl-2-propen-1-amine derivative (1996) Microbios, 85, pp. 83-87De Jaham, C., Paradis, M., Papich, M.G., Antifungal dermatologic agents: Azoles and allylamines (2000) Comp Contin Ed Pract Veter, 22, pp. 548-550De Reuck, A.V.S., Cameron, M.P., The reversible activation of lysossomes in normal cells and the effect of pathological conditions (1963) Lysossomes, pp. 362-375. , De Reuck AVS, Cameron MP (eds.). Boston: Little, Brown & CoDe Souza, A.O., De Azevedo, M.M.M., Silva, C.L., Durán, N., Morphological analysis of the inclusion complex between 3-(4′-bromo-[1,1′-biphenyl]-4-yl)-3-(4-bromophenyl)-N, N-dimethyl-2-propen-1-amine and b-cyclodextrin (2001) VI Pharmatech, p. 37. , Proceeding DD06De Souza, A.O., Hemerly, F.P., Busollo, A.C., Melo, P.S., Machado, G.M., Miranda, C.C., Santa-Rita, R.M., Duran, N., 3-[4′-bromo-(1,1′-biphenyl)-4-yl]-N, N-dimethyl-3-(2-thienyl)-2-propen-1-amine: Synthesis, cytotoxicity, and leishmanicidal, trypanocidal and antimycobacterial activities (2002) J Antimicrob Chemother, 50, pp. 629-637De Souza, A.O., Júnior, R.R.S., Ferreira-Júlio, J.F., Rodriguez, J.A., Melo, P.S., Haun, M., Sato, D.N., Durán, N., Synthesis, antimycobacterial activities and cytotoxicity on V79 of 3-[4′-Y-(1,1′-biphenyl)-4-yl]-N,N-dimethyl-3-(4-X-phenyl) -2-propen-1-amine derivatives (2001) Eur J Med Chem, 36, pp. 843-850De Souza, A.O., Lima, H.O.S., Andrade Santana, M.H., Durán, N., Silva, C.L., Preparation and characterization of liposomes containing an antimycobacterial diarylpropenamine derivative (2001) Pharmaceutical Congress of the Américas, p. 143. , Proceeding 3115De Souza, A.O., Sato, D.N., Aily, D.C.G., Durán, N., In vitro activity of N,N-dimethyl-2-propen-1-amines against Mycobacterium tuberculosis (1998) J Antimicrob Chemother, 42, pp. 407-408Di Bella, M., Braghiroli, D., Witiak, D.T., Antiallergic and antiulcer drugs (1995) Principles of Medicinal Chemistry. 4 Ed., pp. 416-443. , Foye WO, Lemke TL, Williams DA (eds.). Baltimore: Williams & WilkinksDragos, V., Lunder, M., Lack of efficacy of 6-week treatment with oral terbinafine for tinea capitis due to Microsporum canis in children (1997) Pediatr Dematol, 14, pp. 46-48Dumdei, E., Andersen, J., Igzamide, a metabolite of the marine sponge Plocamissma igzo (1993) J Nat Prod, 56, pp. 792-794Dy, M., Machavoine, F., Lebel, B., Ichikawa, A., Gastinel, L.N., Schneider, E., Interleukin-3 promotes histamine synthesis in hematopoietic progenitors by increasing histidine-decarboxylase messenger-rna expression (1993) Biochem Biophys Res Commun, 192, pp. 167-173Endo, Y., Kikuchi, T., Takeda, Y., Nitta, Y., Rikiishi, H., Kumagai, K.I., GM-CSF G-CSF stimulate the synthesis of histamine and putrescine in the hematopoietic organs in vivo (1992) Imm Lett, 33, pp. 9-14Faergemann, J., Zehender, H., Denouel, J., Millerioux, L., Levels of terbinafine in plasma, stratum corneum, dermis-epidermis (without stratum corneum), sebum, hair and nails during and after 250 mg terbinafine orally once per day for four weeks (1993) Acta Derm Venerol, 73, pp. 305-309Godfraind, T., Kaba, A., Phasic and tonic effects of adrenalin on vascular smooth muscle and their inhibition by pharmacological agents (1969) Arch Int Pharmacodyn Ther, 178, pp. 488-491Hall, H., Ogren, S.O., Effects of antidepressant drugs on histamine-H1 receptors in the brain (1984) Life Sci, 34, pp. 597-605Hansh, C., Leo, A., Hoekman, D., (1995) Exploring QSAR: Hydrophobic, Electronic, and Steric Constants, p. 348. , Washington: ACS professional Reference Book ACSHaroon, T.S., Hussain, I., Aman, S., Jahangir, M., Kazmi, A.H., Sami, A.R., Nagi, A.H., Aziz, R., A randomized double-blind comparative study of terbinafine for 1, 2 and 4 weeks in tinea capitis (1996) Br J Dermatol, 135, pp. 86-88Haroon, T.S., Hussain, I., Mahmood, A., Nagi, A.H., Ahmad, I., Zahid, M., An open clinical pilot study of the efficacy and safety of oral terbinafine in dry non-inflammatory tinea capitis (1992) Br J Dermatol, 126 (39), pp. 47-50Hart, R., Bell-Syer, S.E.M., Crawford, F., Torgerson, D.J., Young, P., Russell, I., Systematic review of topicatreatments for fungal infections of the skin and nails of the feet (1999) Br Med J, 319, pp. 79-82Heinisch, G., Holzer, W., Huber, T., Pyridazines, LVIII [1]: 1-Phenyl-1-pyridazinyl-2-substituted ethenes, synthesis and configuration (1991) Monatsheste für Chemie, 122, pp. 1055-1061Hogberg, T., Ulff, B., Renyi, A.L., Ross, S.B., Synthesis of pyridylallylamines related to zimelidine and their inhibition of neuronal monoamine uptake (1981) J Med Chem, 24, pp. 1499-1507Isaacson, E.I., Central Nervous System Stimulants (1998) Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry. 10th Ed., pp. 471-474. , Delgado JN, Remers WA (eds.). Philadelphia: Lippincott Williams & WilkinsIson, R.R., Casy, A.F., Preparation of alpha-methylhistamine from 1-histidine (1970) J Med Chem, 13, pp. 1027-1027Ison, R.R., Casy, A.F., Structural influences upon antihistamine activity: 3-Amino-1-aryl-1-(2-pyridyl) propenes and related compounds (1971) J Pharm Pharmacol, 23, pp. 848-856Ison, R.R., Franks, F.M., Soh, K.S., Binding of conformationally restricted antihistamines to histamine receptors (1973) J Pharm Pharmacol, 25, pp. 887-894Jones, G., Maisey, R.F., Somerville, A.R., Whittle, B.A., Substituted 1,1-diphenyl-3-aminoprop-1-enes and 1,1-diphenyl-3-aminopropanes as potential antidepressant agents (1971) J Med Chem, 14, pp. 161-164Kamatani, Y., Minakata, H., Kenny, P.T.M., Iwashita, T., Watanabe, K., Funase, K., Sun, X.P., Nomoto, K., Achatin-i, an endogenous neuroexcitatory tetrapeptide from achatina-fulica ferussac containing a d-amino-acid residue (1989) Biochem Biophys Res Comm, 160, pp. 1015-1020Katz, A.S., Topical antifungal agents (2000) Curr Problems Dermatol-US, 12, pp. 226-229Kayser, O., Kiderlen, A.F., Laatsch, H., Croft, S.L., In vitro leishmanicidal activity of monomeric and dimeric naphthoquinones (2000) Acta Tropica, 77, pp. 307-314Kim, K.H., Takeuchi, H., Kamatani, Y., Minakata, H., Nomoto, K., Slow inward current induced by achatin-i, an endogenous peptide with a d-phe residue (1991) Eur J Pharm, 194, pp. 99-106Kim, K.H., Takeuchi, H., Kamatani, Y., Minakata, H., Nomoto, K., Structure-activity relationship studies on the endogenous neuroactive tetrapeptide achatin-i on giant-neurons of achatina-fulica ferussac (1991) Life Sci, 48, pp. PL91-PL96Kullavanijaya, P., Reangchainam, S., Ungpakorn, R., Randomized single-blind study of efficacy and tolerability of terbinafine in the treatment of tinea capitis (1997) J Am Acad Dermatol, 37, pp. 272-273LaBella, F.S., Queen, G.M., Brandes, L.J., Interactive binding at cytochrome P-450 of cell growth regulatory bioamines, steroid hormones, antihormones, and drugs (2000) J Cell Biochem, 76, pp. 686-694Lucki, I., Singh, A., Kreiss, D.S., Antidepressant-like behavioral effects of serotonin receptor agonists (1994) Neurosci Biobehav Rev, 18, pp. 85-95Mann, R.D., Pearce, G.L., Dunn, N., Shakir, S., Sedation with "non-sedating" antihistamines: Four prescription-event monitoring studies in general practice (2000) Br Med J, 320, pp. 1184-1186Marsden, P.D., Sampaio, R.N.R., Carvalho, E.M., Veiga, J.P.T., Costa, J.L.M., Llanoscuentas, E.A., High continuous antimony therapy in 2 patients with unresponsive mucosal leishmaniasis (1985) American J Trop Medicine and Hygiene, 34, pp. 710-713Martin, A.R., Anti-infective Agents (1998) Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry. 10th Edition, pp. 185-186. , Delgado JN, Remers WA (eds.). Philadelphia: Lippincott Williams & WilkinsMaxwell, R.A., Keenan, P.D., Chaplin, E., Roth, B., Batmanglidj Eckhardt, S., Molecular features affecting the potency of tricyclic antidepressants and structurally related compounds as inhibitors of the uptake of tritiated norepinephrine by rabbit aortic strips (1969) J Pharmacol Exper Ther, 166, pp. 320-329Mitsuhashi, M., Payan, D.G., Functional diversity of histamine and histamine receptors (1992) J Invest Dermatol, 98, pp. 8S-11SNejjam, F., Zagula, M., Cabiac, M.D., Guessous, N., Humbert, H., Lakhdar, H., Pilot study of terbinafine in children suffering from tinea capitis: Evaluation of efficacy, safety and pharmacokinetics (1995) Br J Dermatol, 132, pp. 98-105Nickolas, T.J., Ignatowski, T.A., Reynolds, J.L., Spengler, R.N., Antidepressant drug-induced alterations in neuron-localized tumor necrosis factor-alpha mRNA and alpha(2)-adregenic receptor sensitivity (2001) J Pharmacol Exper Therapeutic, 297, pp. 680-687Niemegeer, C.J.E., Awouters, F., VanNeuten, J.M., De Nollin, S., Janssen, P.A.J., Protection of rats from compound 48/80-induced lethality. A simple test for inhibitors of mast cell-mediated shock (1978) Arch Int Pharmacodyn, 234, pp. 164-176Nussbaumer, P., Petranyi, G., Stutz, A., Synthesis and structure-activity-relationships of Benzo[b]thienylallylamine antimycotics (1991) J Med Chem, 34, pp. 65-73Nussbaumer, P., Ryder, N.S., Stutz, A., Allylamine antimycotics - Recent trends in structure-activity-relationships and syntheses (1991) Pesticide Science, 31, pp. 437-455Ogren, S.O., Ross, S.B., Hall, H., Holm, A.C., Renyi, A.L., The pharmacology of zimelidine: A 5-HT selective reuptake inhibitor (1981) Acta Psychiatr Scand, 290 (SUPPL.), pp. 127-151Oliveira, D.A., De Souza, A.O., Fernandes, A.M.P., Durán, M., Pereira, D.G., Rodriguez, J.A., Melo, P.S., Durán, N., Synthesis of new 2-propen-1-amine derivatives, trypanocide activities and their squalene epoxidase activity inhibition (1997) Mem Inst Oswaldo Cruz, 92, p. 524Oliveira, D.A., Fernandes, A.M.A.P., De Conti, R., Rodriguez, J.A., Haun, M., Souza-Brito, A.R.M., De Castro, S.L., Duran, N., Evaluation of in vitro toxicity of N,N-dimethyl-2-propen-1-amines isomers (1999) Pharmazie, 54, pp. 847-850Pepe, G., Reboul, J.P., Oddon, Y., Relation between psychotonic or sedative activity of tricyclic antidepressant drugs and noradrenaline and serotonin receptor characteristics from conformational and molecular electrostatic potential analysis (1989) Eur J Med Chem, 24, pp. 1-13Pereira, D.G., De Castro, S.L., Durán, N., Activity of N,N-dimethyl-2-propen-1-amine derivatives in mice experimentally infected with Trypanosoma cruzi (1998) Acta Tropica, 69, pp. 205-211Pereira, D.G., De Souza, A.O., Development of new drugs for tropical diseases (2002) Saúde em Revista, pp. 75-84Petranyi, G., Ryder, N.S., Stutz, A., Atlylamine derivatives - New class of synthetic antifungal agents inhibiting fungal squalene epoxidase (1984) Science, 224, pp. 1239-1241Plember van Balen, G., Caron, G., Ermondi, G., Pagliara, A., Grandi, T., Bouchard, G., Fruttero, R., Testa, B., Lipophilicity behaviour of the zwitterionic antihistamine cetirizine in phosphatidylcholine liposomes/water systems (2001) Pharmaceut Res, 18, pp. 694-701Ram, V.J., Goel, A., Shukla, P.K., Kapil, A., Synthesis of thiophenes and thieno[3,2-c]pyran-4-ones as antileishmanial and antifungal agents (1997) Bioorg Med Chem Lett, 7, pp. 3101-3106Ravina, E., Montanes, J.M., Seco, M.C., Calleja, J.M., Synthesis and potential antidepressant activity of some 1-Phenyl-1-(Substituted-2-Benzofuryl)-3-Amino-1-Propenes (1973) Chimica Therapeutica, 8, pp. 185-187Rekker, R.F., Nauta, W.T., Bultsma, T., Waringa, C.G., Integrated QSAR of H1-receptor antagonists (1975) Eur J Med Chem, 10, pp. 557-562Rekker, R.F., Timmerma, H., Harms, A.F., Nauta, W.T., Changes in antihistaminic and anticholinergic activities of diphenhydramine derivatives on quaternization and role of an asymmetric center (1972) Chim Industr-Milan, 7, pp. 279-282Rekker, R.F., Timmerma, H., Harms, A.F., Nauta, W.T., The antihistaminic and anticholinergic activities of optically active diphenhydramine derivatives - The concept of complementarity (1971) Arzneimittelforschung, 21, pp. 688-691Reynolds, J.E.F., (1989) Martindale the Extra Pharmacopoeia, 29th Edition, pp. 443-443. , London: The Pharmaceutical PressRiley, T.N., DeRuiter, J., Histamine and antihistaminic agents (1998) Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry. 10th Edition, pp. 657-686. , Delgado JN, Remers WA (eds.). Philadelphia: Lippincott Williams & WilkinsRoss, S.B., Renyi, A.L., Inhibition of the neuronal uptake of 5-hydroxytryptamine and noradrenaline in rat brain by (Z) and (E)-3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridyl) allylamines and their secondary analogues (1977) Neuropharmacol, 16, pp. 57-63Ryder, N.S., The mechanism of action of terbinafine (1989) Clin Exp Dermatol, 14, pp. 98-100Salmoiraghi, I., Rossi, M., Valenti, P.D.R.P., Allylamine type xanthone antimycotics (1998) Arch Pharm, 331, pp. 225-227Salunga, T.L., Han, X.Y., Wong, S.M., Takeuchi, H., Matsunami, K., Upton, C., Mercer, A.D., Blocking effects of promethazine, triprolidine and their analogues on the excitation caused by the peptide, achatin-I (1996) Eur J Pharmacol, 304, pp. 163-171Schildkraut, J.J., The catecholamine hypothesis of affective disorders: A review of supporting evidence (1965) Am J Psychiatry, 122, pp. 509-522Stutz, A., Georgopoulos, A., Granitzer, W., Petranyi, G., Berney, D., Synthesis and structure-activity relationships of naphtifine-related allylamine antimycotoics (1986) J Med Chem, 29, pp. 112-125Stütz, A., Allylamines derivatives - A new class of active substances in antifungal chemotherapy (1987) Angew Chem Int Ed Engl, 26, pp. 320-328Szeberenyi, J.B., Pallinger, E., Zsinko, M., Pos, Z., Rothe, G., Orso, E., Szeberenyi, S., Laszlo, V., Inhibition of effects of endogenously synthetized hustamine disturbs in vitro human dendritic cell differentiation (2001) Immunol Lett, 76, pp. 175-182Terlaak, A.M., Vandrooge, M.J., Timmerman, H., Denkelder, G.M.D., QSAR molecular modeling studies on histamine H-1-receptor antagonists (1992) Quantitative Structure-Activity Relationships, 11, pp. 348-363Valderrama, J., Fournet, A., Valderrama, C., Bastias, S., Astudillo, C., De Arias, A.R., Inchausti, A., Yaluff, G., Synthesis and in vitro antiprotozoal activity of thiophene ring-containing quinones (1999) Chem Pharmaceutical Bull, 47, pp. 1221-1226Waringa, C.G., Nauta, W.T., 1,1-Diaryl-3-aminopropenes and some related compounds I (1975) Eur J Med Chem, 10, pp. 349-352Waringa, C.G., Rekker, R.F., Nauta, W.T., 1,1-Diaryl-3-aminopropenes and some related compounds II (1975) Eur J Med Chem, 10, pp. 343-348Watanabe, T., Yamatodani, A., Maeyama, K., Wada, H., Pharmacology of alpha-fluoromethylhistidine, a specific inhibitor of histidine decarboxylase (1990) Trends Pharmacol Sci, 11, pp. 363-367White, A.C., Green, A.F., Hudson, A., Some pharmacological properties of 3-3-diphenyl-propanolamines, 3-3-diphenyl-allylamines, and 3-3-diphenyl-propylamines (1951) Br J Pharmacol Chemother, 6, pp. 560-57