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Volumn 47, Issue 12, 2004, Pages 3220-3235

Synthesis and structure-activity studies on N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an imidazole-containing α1A-adrenoceptor agonist

(33)  Altenbach, Robert J a   Khilevich, Albert a,b   Kolasa, Teodozyj a   Rohde, Jeffrey J a   Bhatia, Pramila A a   Patel, Meena V a   Searle, Xenia B a   Yang, Fan a,c   Bunnelle, William H a   Tietje, Karin a   Bayburt, Erol K a   Carroll, William A a   Meyer, Michael D a   Henry, Rodger a   Buckner, Steven A a   Kuk, Jane a   Daza, Anthony V a   Milicic, Ivan V a   Cain, John C a   Kang, Chae H a   more..


Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 (2,5 DIMETHOXYPHENYL)ETHANOL; ALPHA 1 ADRENERGIC RECEPTOR STIMULATING AGENT; ALPHA 1A ADRENERGIC RECEPTOR; ALPHA 1A ADRENERGIC RECEPTOR STIMULATING AGENT; ALPHA 1B ADRENERGIC RECEPTOR; ALPHA 1D ADRENERGIC RECEPTOR; ALPHA 2A ADRENERGIC RECEPTOR; ALPHA 2B ADRENERGIC RECEPTOR; IMIDAZOLE DERIVATIVE; N [5 (1H IMIDAZOL 4 YL) 5,6,7,8 TETRAHYDRO 1 NAPHTHALENYL]METHANESULFONAMIDE; PHENYLPROPANOLAMINE; UNCLASSIFIED DRUG;

EID: 2542587862     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030551a     Document Type: Article
Times cited : (8)

References (75)
  • 2
    • 0027501903 scopus 로고
    • Pharmacology of lower urinary tract smooth muscles and penile erectile tissues
    • Andersson, K. E. Pharmacology of Lower Urinary Tract Smooth Muscles and Penile Erectile Tissues. Pharmacol. Rev. 1993, 45, 253-308.
    • (1993) Pharmacol. Rev. , vol.45 , pp. 253-308
    • Andersson, K.E.1
  • 3
    • 0023243159 scopus 로고
    • Phenylpropanolamine in treatment of female stress urinary incontinence. Double-blind placebo controlled study in 24 patients
    • Collste, L.; Lindskog, M. Phenylpropanolamine in treatment of female stress urinary incontinence. Double-blind placebo controlled study in 24 patients. Urology 1987, 30, 398-403.
    • (1987) Urology , vol.30 , pp. 398-403
    • Collste, L.1    Lindskog, M.2
  • 4
    • 0017613066 scopus 로고
    • Treatment of female stress incontinence with midodrine: Preliminary report
    • (a) Jonas, D. Treatment of Female Stress Incontinence with Midodrine: Preliminary Report. J. Urol. 1977, 118, 980-982.
    • (1977) J. Urol. , vol.118 , pp. 980-982
    • Jonas, D.1
  • 5
    • 0022916685 scopus 로고
    • Midodrine for female incontinence: A preliminary report
    • (b) Garofalo, F.; Lalanne, G. M.; Nanni, G. Midodrine for Female Incontinence: A Preliminary Report. Clin. Ther. 1986, 9, 44-46.
    • (1986) Clin. Ther. , vol.9 , pp. 44-46
    • Garofalo, F.1    Lalanne, G.M.2    Nanni, G.3
  • 6
    • 0028198502 scopus 로고
    • Clinical effect of midodrine hydrochloride on the patients with urinary incontinence
    • (c) Nito, H. Clinical effect of midodrine hydrochloride on the patients with urinary incontinence. Hinyokika Kiyo 1994, 40, 91-94.
    • (1994) Hinyokika Kiyo , vol.40 , pp. 91-94
    • Nito, H.1
  • 8
    • 0021019213 scopus 로고
    • The effect of midodrine and its active metabolite ST 1059 on the human urethra in vitro and in vivo
    • (e) Andersson, K. E.; Ekman, G.; Henriksson, L.; Ulmsten, U. The effect of midodrine and its active metabolite ST 1059 on the human urethra in vitro and in vivo. Scand. J. Urol. Nephrol. 1983, 17, 261-265.
    • (1983) Scand. J. Urol. Nephrol. , vol.17 , pp. 261-265
    • Andersson, K.E.1    Ekman, G.2    Henriksson, L.3    Ulmsten, U.4
  • 9
    • 0031608212 scopus 로고    scopus 로고
    • Midodrine. A review of its therapeutic use in the management of orthostatic hypotension
    • (a) McClellan, K. J.; Wiseman, L. R.; Wilde, M. I. Midodrine. A Review of Its Therapeutic Use in the Management of Orthostatic Hypotension. Drugs Aging 1998, 12, 76-86.
    • (1998) Drugs Aging , vol.12 , pp. 76-86
    • McClellan, K.J.1    Wiseman, L.R.2    Wilde, M.I.3
  • 11
    • 2542528774 scopus 로고    scopus 로고
    • Treatment of stress urinary incontinence
    • Appell, R. A., Ed.; Humana Press: Totowa, NJ
    • (c) Rackley, R. Treatment of Stress Urinary Incontinence. In Voiding Dysfunction: Diagnosis and Treatment; Appell, R. A., Ed.; Humana Press: Totowa, NJ, 2000; pp 163-184.
    • (2000) Voiding Dysfunction: Diagnosis and Treatment , pp. 163-184
    • Rackley, R.1
  • 14
    • 0031596558 scopus 로고    scopus 로고
    • Quantification and distribution of alpha1-adrenoceptor subtype mRNAs in human proximal urethra
    • Nasu, K.; Moriyama, N.; Fukasawa, R.; Tsujimoto, G.; Tanaka, T.; Yano, J.; Kawabe, K. Quantification and Distribution of Alpha1-Adrenoceptor Subtype mRNAs in human proximal urethra. Br. J. Pharmacol. 1998, 123, 1289-1293.
    • (1998) Br. J. Pharmacol. , vol.123 , pp. 1289-1293
    • Nasu, K.1    Moriyama, N.2    Fukasawa, R.3    Tsujimoto, G.4    Tanaka, T.5    Yano, J.6    Kawabe, K.7
  • 15
    • 0030447950 scopus 로고    scopus 로고
    • Effects of selective and nonselective alpha-1-adrenoceptor antagonists on intraurethral and arterial pressures in intact conscious dogs
    • Brune, M. E.; Katwala, S. P.; Milicic, I.; Buckner, S. A.; Ireland, L. M.; Kerwin, J. F.; Hancock, A. A. Effects of Selective and Nonselective Alpha-1-Adrenoceptor Antagonists on Intraurethral and Arterial Pressures in Intact Conscious Dogs. Pharmacology 1996, 53, 356-368.
    • (1996) Pharmacology , vol.53 , pp. 356-368
    • Brune, M.E.1    Katwala, S.P.2    Milicic, I.3    Buckner, S.A.4    Ireland, L.M.5    Kerwin, J.F.6    Hancock, A.A.7
  • 16
    • 7144228623 scopus 로고    scopus 로고
    • Actions of A-131701, a novel, selective antagonist for alpha-1a compared with alpha-1b adrenoceptors on intraurethral and blood pressure responses in conscious dogs and a pharmacodynamic assessment of in vivo prostatic selectivity
    • Hancock, A. A.; Brune, M. E.; Witte, D. G.; Marsh, K. C.; Katwala, S.; Milicic, I.; Ireland, L. M.; Crowell, D.; Meyer, M. D.; Kerwin, J. F. Actions of A-131701, a Novel, Selective Antagonist for Alpha-1A Compared with Alpha-1B Adrenoceptors on Intraurethral and Blood Pressure Responses in Conscious Dogs and a Pharmacodynamic Assessment of in Vivo Prostatic Selectivity. J. Pharmacol. Exp. Ther. 1998, 285, 628-642.
    • (1998) J. Pharmacol. Exp. Ther. , vol.285 , pp. 628-642
    • Hancock, A.A.1    Brune, M.E.2    Witte, D.G.3    Marsh, K.C.4    Katwala, S.5    Milicic, I.6    Ireland, L.M.7    Crowell, D.8    Meyer, M.D.9    Kerwin, J.F.10
  • 17
    • 0034037332 scopus 로고    scopus 로고
    • Adrenoceptor subclassification: An approach to improved cardiovascular therapeutics
    • Hieble, J. P. Adrenoceptor subclassification: an approach to improved cardiovascular therapeutics. Pharm. Acta Helv. 2000, 74, 163-171.
    • (2000) Pharm. Acta Helv. , vol.74 , pp. 163-171
    • Hieble, J.P.1
  • 20
    • 0032724573 scopus 로고    scopus 로고
    • Vascular alpha(1D)-adrenoceptors: Are they related to hypertension?
    • (b) Villalobos-Molina, R.; Ibarra, M. Vascular Alpha(1D)-Adrenoceptors: Are They Related to Hypertension?. Arch. Med. Res. 1999, 30, 347-352.
    • (1999) Arch. Med. Res. , vol.30 , pp. 347-352
    • Villalobos-Molina, R.1    Ibarra, M.2
  • 21
    • 0037183775 scopus 로고    scopus 로고
    • Transgenic studies of alpha(1)-adrenergic receptor subtype function
    • Tanoue, A.; Koshimizu, T.; Tsujimoto, G. Transgenic studies of alpha(1)-adrenergic receptor subtype function. Life Sci. 2002, 71, 2207-2215.
    • (2002) Life Sci. , vol.71 , pp. 2207-2215
    • Tanoue, A.1    Koshimizu, T.2    Tsujimoto, G.3
  • 26
    • 33751500012 scopus 로고
    • A facile route to imidazol-4-yl anions and their reaction with carbonyl compounds
    • Turner, R. M.; Lindell, S. D.; Ley, S. V. A facile route to imidazol-4-yl anions and their reaction with carbonyl compounds. J. Org. Chem. 1991, 56, 5739-5740.
    • (1991) J. Org. Chem. , vol.56 , pp. 5739-5740
    • Turner, R.M.1    Lindell, S.D.2    Ley, S.V.3
  • 27
    • 0043114499 scopus 로고
    • 4-Lithio-1-tritylimidazole as a synthetic intermediate. Synthesis of imidazole-4-carboxaldehyde
    • Kirk, K. L. 4-Lithio-1-tritylimidazole as a synthetic intermediate. Synthesis of imidazole-4-carboxaldehyde. J. Heterocycl. Chem. 1985, 22, 57-59.
    • (1985) J. Heterocycl. Chem. , vol.22 , pp. 57-59
    • Kirk, K.L.1
  • 28
    • 0028981111 scopus 로고
    • A-61603, a potent alpha 1-adrenergic receptor agonist, selective for the alpha 1A receptor subtype
    • 3H]-prazosin were run as previously described: Knepper, S. M.; Buckner, S. A.; Brune, M. E.; DeBernardis, J. F.; Meyer, M. D.; Hancock, A. A. A-61603, a Potent Alpha 1-Adrenergic Receptor Agonist, Selective for the Alpha 1A Receptor Subtype. J. Pharmacol. Exp. Ther. 1995, 274, 97-103.
    • (1995) J. Pharmacol. Exp. Ther. , vol.274 , pp. 97-103
    • Knepper, S.M.1    Buckner, S.A.2    Brune, M.E.3    DeBernardis, J.F.4    Meyer, M.D.5    Hancock, A.A.6
  • 29
    • 0029585887 scopus 로고
    • Actions of terazosin and its enantiomers at subtypes of alpha 1- and alpha 2-adrenoceptors in vitro
    • 3H]-rauwolscine were run as previously described: Hancock, A. A.; Buckner, S. A.; Ireland, L. M.; Knepper, S. M.; Kerwin, J. F., Jr. Actions of terazosin and its enantiomers at subtypes of alpha 1- and alpha 2-adrenoceptors in vitro. J. Recept. Signal Transduction Res. 1995, 15, 863-885.
    • (1995) J. Recept. Signal Transduction Res. , vol.15 , pp. 863-885
    • Hancock, A.A.1    Buckner, S.A.2    Ireland, L.M.3    Knepper, S.M.4    Kerwin Jr., J.F.5
  • 30
    • 2542545318 scopus 로고    scopus 로고
    • note
    • 2C has not been shown to play a role in control of blood pressure.
  • 31
    • 0034747422 scopus 로고    scopus 로고
    • The alpha(2)-adrenergic receptors in hypertension and heart failure: Experimental and clinical studies
    • (b) Gavras, I.; Manolis, A. J.; Gavras, H. The alpha(2)-adrenergic receptors in hypertension and heart failure: experimental and clinical studies. J. Hypertens. 2001, 19, 2115-2124.
    • (2001) J. Hypertens. , vol.19 , pp. 2115-2124
    • Gavras, I.1    Manolis, A.J.2    Gavras, H.3
  • 33
    • 0027509730 scopus 로고
    • Investigation of the subtypes of alpha 1-adrenoceptor mediating contractions of rat aorta, vas deferens and spleen
    • (b) Aboud, R.; Shafii, M.; Docherty, J. R. Investigation of the subtypes of alpha 1-adrenoceptor mediating contractions of rat aorta, vas deferens and spleen. Br. J. Pharmacol. 1993, 109, 80-87.
    • (1993) Br. J. Pharmacol. , vol.109 , pp. 80-87
    • Aboud, R.1    Shafii, M.2    Docherty, J.R.3
  • 34
    • 2542543822 scopus 로고    scopus 로고
    • note
    • 2 = 5.08 ± 0.11, 22% efficacy.
  • 35
    • 0034837482 scopus 로고    scopus 로고
    • Comparison of alpha1-adrenoceptor agonists in canine urethral pressure profilometry and abdominal leak point pressure models
    • Brune, M. E.; O'Neill, A. B.; Gauvin, D. M.; Katwala, S. P.; Altenbach, R. J.; Brioni, J. D.; Hancock, A. A.; Sullivan, J. P. Comparison of alpha1-adrenoceptor agonists in canine urethral pressure profilometry and abdominal leak point pressure models. J. Urol. 2001, 166, 1555-1559.
    • (2001) J. Urol. , vol.166 , pp. 1555-1559
    • Brune, M.E.1    O'Neill, A.B.2    Gauvin, D.M.3    Katwala, S.P.4    Altenbach, R.J.5    Brioni, J.D.6    Hancock, A.A.7    Sullivan, J.P.8
  • 36
    • 2542606386 scopus 로고    scopus 로고
    • note
    • Measurements were made within 1 min of dosing to alleviate any pharmacokinetics effects.
  • 37
    • 2542533314 scopus 로고    scopus 로고
    • note
    • 2O (a 15% increase over baseline) and resulted in a significant decrease in leakage episodes from 5 per 24 h to 2 per 24 h.
  • 38
    • 2542525680 scopus 로고    scopus 로고
    • note
    • (b) In the in vivo dog model, the baseline pressure measurement is of the catheter balloon pressure and was measured at approximately 400 mmHg. This is not physiologic but due to the elastic forces in the inflated balloon. The IUP measurement was recorded as the net change in pressure above this baseline pressure. From profilometry experiments (data not shown), the measured urethral pressure (the PUCP or proximal urethral closure pressure) that corresponds to the location of the balloon catheter in the in vivo dog model was 4-5 mmHg. Therefore, a 5 mmHg increase in IUP is approximately a 100% increase over physiological baseline urethral pressure.
  • 39
    • 2542610970 scopus 로고    scopus 로고
    • note
    • The 20 mmHg increase in MAP was chosen as a consistently measurable response above the noise of the assay. The average baseline MAP values in the anesthetized dogs were about 80 mmHg. Therefore, a 20 mmHg increase in MAP represents approximately a 25% increase over baseline.
  • 41
    • 2542610973 scopus 로고    scopus 로고
    • note
    • A boost in potency going from tetralin to indane has been observed previously. See ref 28.
  • 43
    • 0034797955 scopus 로고    scopus 로고
    • The role of alpha(1)-adrenergic receptor subtypes in lower urinary tract symptoms
    • (a) Schwinn, D. A. The role of alpha(1)-adrenergic receptor subtypes in lower urinary tract symptoms. BJU Int. 2001 88 (Suppl. 2), 27-34.
    • (2001) BJU Int. , vol.88 , Issue.SUPPL. 2 , pp. 27-34
    • Schwinn, D.A.1
  • 44
    • 12244305522 scopus 로고    scopus 로고
    • The alpha(1)-adrenoceptor profile in human skeletal muscle resistance arteries in critical limb ischaemia
    • (b) Jarajapu, Y. P. R.; McGrath, J. C.; Hillier, C.; MacDonald, A. The alpha(1)-adrenoceptor profile in human skeletal muscle resistance arteries in critical limb ischaemia. Cardiovasc. Res. 2003, 57, 554-562.
    • (2003) Cardiovasc. Res. , vol.57 , pp. 554-562
    • Jarajapu, Y.P.R.1    McGrath, J.C.2    Hillier, C.3    MacDonald, A.4
  • 45
    • 0035933408 scopus 로고    scopus 로고
    • The alpha(1A)-adrenoceptor subtype mediates contraction in rat femoral resistance arteries
    • (a) Jarajapu, Y. P. R.; Hillier, C.; MacDonald, A. The alpha(1A)-adrenoceptor subtype mediates contraction in rat femoral resistance arteries. Eur. J. Pharmacol. 2001, 422, 127-135.
    • (2001) Eur. J. Pharmacol. , vol.422 , pp. 127-135
    • Jarajapu, Y.P.R.1    Hillier, C.2    MacDonald, A.3
  • 46
    • 0029905021 scopus 로고    scopus 로고
    • Pharmacological characterization of alpha1-adrenoceptor subtype mediating regulation of arterial pressure and urethral perfusion pressure in the anesthetized rat
    • (b) Guilmard, C.; Auguet, M.; Chabrier, P. E. Pharmacological characterization of alpha1-adrenoceptor subtype mediating regulation of arterial pressure and urethral perfusion pressure in the anesthetized rat. J. Auton. Pharmacol. 1996, 16, 197-203.
    • (1996) J. Auton. Pharmacol. , vol.16 , pp. 197-203
    • Guilmard, C.1    Auguet, M.2    Chabrier, P.E.3
  • 47
    • 0033847632 scopus 로고    scopus 로고
    • Role of the postsynaptic alpha(2)-adrenergic receptor subtypes in catecholamine-induced vasoconstriction
    • Duka, I.; Gavras, I.; Johns, C.; Handy, D. E.; Gavras, H. Role of the postsynaptic alpha(2)-adrenergic receptor subtypes in catecholamine-induced vasoconstriction. Gen. Pharmacol. 2000, 34, 101-106.
    • (2000) Gen. Pharmacol. , vol.34 , pp. 101-106
    • Duka, I.1    Gavras, I.2    Johns, C.3    Handy, D.E.4    Gavras, H.5
  • 48
    • 0034999544 scopus 로고    scopus 로고
    • Vascular adrenoceptors: An update
    • (a) Guimaraes, S.; Moura, D. Vascular adrenoceptors: An update. Pharmacol. Rev. 2001, 53, 319-356.
    • (2001) Pharmacol. Rev. , vol.53 , pp. 319-356
    • Guimaraes, S.1    Moura, D.2
  • 49
    • 0034087475 scopus 로고    scopus 로고
    • In vivo gene modification elucidates subtype-specific functions of alpha(2)-adrenergic receptors
    • (b) Kable, J. W.; Murrin, L. C.; Bylund, D. B. In vivo gene modification elucidates subtype-specific functions of alpha(2)-adrenergic receptors. J. Pharmacol. Exp. Ther. 2000, 293, 1-7.
    • (2000) J. Pharmacol. Exp. Ther. , vol.293 , pp. 1-7
    • Kable, J.W.1    Murrin, L.C.2    Bylund, D.B.3
  • 50
    • 0030844448 scopus 로고    scopus 로고
    • Gene targeting-homing in on alpha 2-adrenoceptor-subtype function
    • (c) MacDonald, E.; Kobilka, B. K.; Scheinin, M. Gene targeting-homing in on alpha 2-adrenoceptor-subtype function. Trends Pharmacol. Sci. 1997, 18, 211-219.
    • (1997) Trends Pharmacol. Sci. , vol.18 , pp. 211-219
    • MacDonald, E.1    Kobilka, B.K.2    Scheinin, M.3
  • 51
    • 2542514950 scopus 로고    scopus 로고
    • note
    • 2 value, slope, and number of compounds/plot (n) are shown in Tables 8 and 9.
  • 52
    • 0030807197 scopus 로고    scopus 로고
    • Characterization of alpha 2-adrenoceptors mediating contraction of dog saphenous vein: Identity with the human alpha 2A subtype
    • (a) MacLennan, S. J.; Luong, L. A.; Jasper, J. R.; To, Z. P.; Eglen, R. M. Characterization of alpha 2-adrenoceptors mediating contraction of dog saphenous vein: identity with the human alpha 2A subtype. Br. J. Pharmacol. 1997, 121, 1721-1729.
    • (1997) Br. J. Pharmacol. , vol.121 , pp. 1721-1729
    • MacLennan, S.J.1    Luong, L.A.2    Jasper, J.R.3    To, Z.P.4    Eglen, R.M.5
  • 54
    • 0027320952 scopus 로고
    • Presynaptic alpha 2-autoreceptors in brain cortex: Alpha 2D in the rat and alpha 2A in the rabbit
    • (a) Trendelenburg, A. U.; Limberger, N.; Starke, K. Presynaptic alpha 2-autoreceptors in brain cortex: alpha 2D in the rat and alpha 2A in the rabbit. Naunyn-Schmiedeberg's Arch. Pharmacol. 1993, 348, 35-45.
    • (1993) Naunyn-Schmiedeberg's Arch. Pharmacol. , vol.348 , pp. 35-45
    • Trendelenburg, A.U.1    Limberger, N.2    Starke, K.3
  • 56
    • 1642538361 scopus 로고    scopus 로고
    • Pharmacological characteristics of Ro 115-1240, a selective alpha1A/1L-adrenoceptor partial agonist: A potential therapy for stress urinary incontinence
    • (a) Blue, D. R.; Daniels, D. V.; Gever, J. R.; Jett, M. F.; O'Yang, C.; Tang, H. M.; Williams, T. J.; Ford, A. P. D. W. Pharmacological characteristics of Ro 115-1240, a selective alpha1A/1L-adrenoceptor partial agonist: a potential therapy for stress urinary incontinence. BJU Int. 2004, 93, 162-170.
    • (2004) BJU Int. , vol.93 , pp. 162-170
    • Blue, D.R.1    Daniels, D.V.2    Gever, J.R.3    Jett, M.F.4    O'Yang, C.5    Tang, H.M.6    Williams, T.J.7    Ford, A.P.D.W.8
  • 57
    • 1642538369 scopus 로고    scopus 로고
    • A randomized crossover study to evaluate Ro 115-1240, a selective alpha1A/1L-adrenoceptor partial agonist in women with stress urinary incontinence
    • (b) Musselman, D. M.; Ford, A. P. D. W.; Gennevois, D. J.; Harbison, M. L.; Laurent, L.; Mokatrin, A. S.; Stoltz, R. R.; Blue, D. R. A randomized crossover study to evaluate Ro 115-1240, a selective alpha1A/1L-adrenoceptor partial agonist in women with stress urinary incontinence. BJU Int. 2004, 93, 78-83.
    • (2004) BJU Int. , vol.93 , pp. 78-83
    • Musselman, D.M.1    Ford, A.P.D.W.2    Gennevois, D.J.3    Harbison, M.L.4    Laurent, L.5    Mokatrin, A.S.6    Stoltz, R.R.7    Blue, D.R.8
  • 58
    • 0001042238 scopus 로고
    • Chirochromism-photochromism by epimerization: Search for a liquid crystal phototrigger
    • Zhang, M.; Schuster, G. B. Chirochromism-Photochromism by Epimerization: Search for a Liquid Crystal Phototrigger. J. Am. Chem. Soc, 1994, 116, 4852-4857.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4852-4857
    • Zhang, M.1    Schuster, G.B.2
  • 59
    • 0042100363 scopus 로고
    • Concerning lone-pair stereospecificity of intramolecular OH hydrogen bonds to oxygen and sulfur in solution
    • Schaefer, T.; McKinnon, D. M.; Sebastian, R.; Peeling, J.; Penner, G. H. ; Veregin, R. P. Concerning lone-pair stereospecificity of intramolecular OH hydrogen bonds to oxygen and sulfur in solution. Can. J. Chem. 1987, 65, 908-914.
    • (1987) Can. J. Chem. , vol.65 , pp. 908-914
    • Schaefer, T.1    McKinnon, D.M.2    Sebastian, R.3    Peeling, J.4    Penner, G.H.5    Veregin, R.P.6
  • 60
    • 0030890290 scopus 로고    scopus 로고
    • Structure-activity studies for a novel series of N-(arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines possessing dual 5-HT uptake inhibiting and α2-antagonistic activities
    • 5-Methanesulfonamido-1-tetralone (4G) was N-benzylated to provide N-benzyl-N-(5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)-methanesulfonamide (4I) as in example 26 of the following reference: Meyer, M. D.; Hancock, A. A.; Tietje, K.; Sippy, K. B.; Prasad, R.; Stout, D. M.; Arendsen, D. L.; Donner, B. G.; Carroll, W. A. Structure-activity studies for a novel series of N-(arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines possessing dual 5-HT uptake inhibiting and α2-antagonistic activities. J. Med. Chem. 1997, 40, 1049-1062.
    • (1997) J. Med. Chem. , vol.40 , pp. 1049-1062
    • Meyer, M.D.1    Hancock, A.A.2    Tietje, K.3    Sippy, K.B.4    Prasad, R.5    Stout, D.M.6    Arendsen, D.L.7    Donner, B.G.8    Carroll, W.A.9
  • 61
    • 0006336965 scopus 로고
    • Organic sulfur mechanisms. 36. Cyclopropanesulfonyl chloride: Its mechanisms of hydrolysis and reactions with tertiary amines in organic media
    • King, J. F.; Joe, Y. L.; Lam, J. Y. L.; Ferrazzi, G. Organic sulfur mechanisms. 36. Cyclopropanesulfonyl chloride: its mechanisms of hydrolysis and reactions with tertiary amines in organic media. J. Org. Chem. 1993, 58, 1128-1135.
    • (1993) J. Org. Chem. , vol.58 , pp. 1128-1135
    • King, J.F.1    Joe, Y.L.2    Lam, J.Y.L.3    Ferrazzi, G.4
  • 62
    • 0018831750 scopus 로고
    • Synthesis of 2-fluoro-7,12-dimethylbenz[a]anthracene
    • Newman, M. S.; Tuncay, A. Synthesis of 2-fluoro-7,12-dimethylbenz[a]anthracene. J. Org. Chem. 1980, 45, 348-349.
    • (1980) J. Org. Chem. , vol.45 , pp. 348-349
    • Newman, M.S.1    Tuncay, A.2
  • 63
    • 0025768438 scopus 로고
    • Synthesis of 6/7-halotetralones
    • Owton, W. M.; Brunavs, M. Synthesis of 6/7-halotetralones. Synth. Commun. 1991, 21, 981-987.
    • (1991) Synth. Commun. , vol.21 , pp. 981-987
    • Owton, W.M.1    Brunavs, M.2
  • 64
    • 0035705141 scopus 로고    scopus 로고
    • Hydrocarbon humps in the marine environment: Synthesis, toxicity, and aqueous solubility of monoaromatic compounds
    • Smith, E.; Wraige, E.; Donkin, P.; Rowland, S. Hydrocarbon humps in the marine environment: Synthesis, toxicity, and aqueous solubility of monoaromatic compounds. Environ. Toxicol. Chem. 2001, 20, 2428-2432.
    • (2001) Environ. Toxicol. Chem. , vol.20 , pp. 2428-2432
    • Smith, E.1    Wraige, E.2    Donkin, P.3    Rowland, S.4
  • 65
    • 0019187186 scopus 로고
    • Total synthesis of ring-c aromatic 18-nor steroid
    • Chatterjee, A.; Hazra, B. G. Total synthesis of ring-c aromatic 18-nor steroid. Tetrahedron 1980, 36, 2513-2520.
    • (1980) Tetrahedron , vol.36 , pp. 2513-2520
    • Chatterjee, A.1    Hazra, B.G.2
  • 66
    • 0012011416 scopus 로고
    • A short synthesis of tetrahydrobenzisoindolines
    • De, B.; DeBernardis, J. F.; Prasad, R. A short synthesis of tetrahydrobenzisoindolines, Synth. Commun. 1988, 18, 481-485.
    • (1988) Synth. Commun. , vol.18 , pp. 481-485
    • De, B.1    DeBernardis, J.F.2    Prasad, R.3
  • 68
    • 0021331996 scopus 로고
    • Synthesis and β-adrenergic blocking activity of 2-(N-substituted amino)-1,2,3,4-tetrahydronaphthalen-1-ol derivatives
    • Itoh, K.; Miyake, A.; Tada, N.; Hirata, M.; Oka, Y. Synthesis and β-adrenergic blocking activity of 2-(N-substituted amino)-1,2,3,4-tetrahydronaphthalen-1-ol derivatives. Chem. Pharm. Bull. 1984, 32, 130-151.
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 130-151
    • Itoh, K.1    Miyake, A.2    Tada, N.3    Hirata, M.4    Oka, Y.5
  • 69
    • 0015797794 scopus 로고
    • Trimethylammonium phenyl ketones. Actions on the cholinergic receptor and acetylcholinesterase
    • Hasbun, J. A.; Barker, K. K.; Mertes, M. P. Trimethylammonium phenyl ketones. Actions on the cholinergic receptor and acetylcholinesterase. J. Med. Chem. 1973, 16, 847-849.
    • (1973) J. Med. Chem. , vol.16 , pp. 847-849
    • Hasbun, J.A.1    Barker, K.K.2    Mertes, M.P.3
  • 70
    • 0022344784 scopus 로고
    • 4-[2-(Di-n-propylamino)ethyl]-2(3H)-indolone: A prejunctional dopamine receptor agonist
    • Gallagher, G.; Lavanchy, P. G.; Wilson, J. W.; Hieble, J. P.; DeMarinis, R. M. 4-[2-(Di-n-propylamino)ethyl]-2(3H)-indolone: a prejunctional dopamine receptor agonist. J. Med. Chem. 1985, 28, 1533-1536.
    • (1985) J. Med. Chem. , vol.28 , pp. 1533-1536
    • Gallagher, G.1    Lavanchy, P.G.2    Wilson, J.W.3    Hieble, J.P.4    DeMarinis, R.M.5
  • 71
    • 0038434741 scopus 로고
    • Pyrones. I. Attempted oxidation of chromanones with selenium dioxide
    • Chakravarti, D.; Dutta, J. Pyrones. I. Attempted oxidation of chromanones with selenium dioxide. J. Indian Chem. Soc. 1939, 16, 639-644.
    • (1939) J. Indian Chem. Soc. , vol.16 , pp. 639-644
    • Chakravarti, D.1    Dutta, J.2
  • 72
    • 84986992078 scopus 로고
    • Synthesis of new N,N,1,1-tetramethylisobenzofuranamines
    • Stanetty, P.; Rodler, I.; Krumpak, B. Synthesis of new N,N,1,1-tetramethylisobenzofuranamines. J. Prakt. Chem. 1993, 335, 17-22.
    • (1993) J. Prakt. Chem. , vol.335 , pp. 17-22
    • Stanetty, P.1    Rodler, I.2    Krumpak, B.3
  • 73
    • 0027983781 scopus 로고
    • Synthesis of 4,4′-Biimidazoles
    • Cliff, M. D.; Pyne, S. G. Synthesis of 4,4′-Biimidazoles. Synthesis 1994, 7, 681-682.
    • (1994) Synthesis , vol.7 , pp. 681-682
    • Cliff, M.D.1    Pyne, S.G.2


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