메뉴 건너뛰기




Volumn 40, Issue 18, 1997, Pages 2895-2901

Total syntheses and anticholinesterase activities of (3aS)-N(8)- norphysostigmine, (3aS)-N(8)-norphenserine, their antipodal isomers, and other N(8)-substituted analogues

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINESTERASE INHIBITOR; N(8) BENZYLESERMETHOLE; N(8) NORPHENSERINE; N(8) NORPHYSOSTIGMINE; UNCLASSIFIED DRUG;

EID: 0030758320     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970210v     Document Type: Article
Times cited : (59)

References (27)
  • 2
    • 0028894072 scopus 로고
    • Phenserine and Ring C Hetero-Analogues: Drug Candidates for Treatment of Alzheimer's Disease
    • Greig, N. H.; Pei, X. F.; Soncrant, T. T.; Ingram, D. K.; Brossi, A. Phenserine and Ring C Hetero-Analogues: Drug Candidates for Treatment of Alzheimer's Disease. Med. Res. Rev. 1995, 15, 3-31.
    • (1995) Med. Res. Rev. , vol.15 , pp. 3-31
    • Greig, N.H.1    Pei, X.F.2    Soncrant, T.T.3    Ingram, D.K.4    Brossi, A.5
  • 3
    • 0002642999 scopus 로고    scopus 로고
    • Phenserine, a Novel Anticholinesterase Related to Physostigmine: Total Synthesis and Biological Properties
    • Brossi, A.; Pei, X. F.; Greig, N. H. Phenserine, a Novel Anticholinesterase Related to Physostigmine: Total Synthesis and Biological Properties. Aust. J. Chem. 1996, 49, 171-181.
    • (1996) Aust. J. Chem. , vol.49 , pp. 171-181
    • Brossi, A.1    Pei, X.F.2    Greig, N.H.3
  • 5
    • 0000353442 scopus 로고
    • A Chiral Route to Both Enationmers of Physostigmine and the First Synthesis of (-)-Norphysostigmine
    • Takano, S.; Moriya, M.; Iwabuchi, Y.; Ogasawara, K. A Chiral Route to Both Enationmers of Physostigmine and the First Synthesis of (-)-Norphysostigmine. Chem. Lett. 1990, 109-112.
    • (1990) Chem. Lett. , pp. 109-112
    • Takano, S.1    Moriya, M.2    Iwabuchi, Y.3    Ogasawara, K.4
  • 6
    • 0014375345 scopus 로고
    • The Anti-acetylcholinesterase Activities of the Alkaloids of Physostigma venenosum seeds
    • Robinson, B.; Robinson, J. B. The Anti-acetylcholinesterase Activities of The Alkaloids of Physostigma venenosum seeds. J. Pharm. Pharmacol. 1968, 21 (Suppl.), 213s.
    • (1968) J. Pharm. Pharmacol. , vol.21 , Issue.SUPPL.
    • Robinson, B.1    Robinson, J.B.2
  • 9
    • 85016569980 scopus 로고
    • Total synthesis of (-)-Pseudophrynamineol
    • Sun, W. Y.; Sun, Y.; Tang, Y. C.; Hu, J. Q. Total synthesis of (-)-Pseudophrynamineol. Syn. Lett. 1993, 337.
    • (1993) Syn. Lett. , pp. 337
    • Sun, W.Y.1    Sun, Y.2    Tang, Y.C.3    Hu, J.Q.4
  • 10
    • 0000252377 scopus 로고
    • Practical Synthesis of Unnatural (+)-Physostigmine and Carbamate Analogues
    • Yu, Q. S.; Brossi, A. Practical Synthesis of Unnatural (+)-Physostigmine and Carbamate Analogues. Heterocycles 1988, 27, 745.
    • (1988) Heterocycles , vol.27 , pp. 745
    • Yu, Q.S.1    Brossi, A.2
  • 11
    • 0024207217 scopus 로고
    • Synthesis and Anticholinesterase Activity of (-)-N1-Norphysostigmine, (-)-Eseramine, and Other N(1)-Substituted Analogues of (-)-Physostigmine
    • Yu, Q. S.; Atack, J. R.; Rapoport, S. I.; Brossi, A. Synthesis and Anticholinesterase Activity of (-)-N1-Norphysostigmine, (-)-Eseramine, and Other N(1)-Substituted Analogues of (-)-Physostigmine. J. Med. Chem. 1988, 31, 2297-2300.
    • (1988) J. Med. Chem. , vol.31 , pp. 2297-2300
    • Yu, Q.S.1    Atack, J.R.2    Rapoport, S.I.3    Brossi, A.4
  • 12
    • 85008040826 scopus 로고
    • A Simple General Method for the Oxidation of Indoles to Oxiindoles
    • Szabo-Pusztay, K.; Szabo, L. A Simple General Method for the Oxidation of Indoles to Oxiindoles. Synthesis 1979, 276.
    • (1979) Synthesis , pp. 276
    • Szabo-Pusztay, K.1    Szabo, L.2
  • 13
    • 0001756275 scopus 로고
    • Progress Towards a Practical Total Synthesis of Calabar Alkaloids: Total Synthesis of (-)-Esermethol and (-)-Physovenol Methyl Ether from (3S)-1,3-Dimethyl-3-carboxymethyl-5-methoxyoxindole
    • Yu, Q. S.; Luo, W. M.; Li, Y. Q.; Brossi, A. Progress Towards A Practical Total Synthesis of Calabar Alkaloids: Total Synthesis of (-)-Esermethol and (-)-Physovenol Methyl Ether from (3S)-1,3-Dimethyl-3-carboxymethyl-5-methoxyoxindole. Heterocycles 1993, 36, 1279.
    • (1993) Heterocycles , vol.36 , pp. 1279
    • Yu, Q.S.1    Luo, W.M.2    Li, Y.Q.3    Brossi, A.4
  • 14
    • 0025011968 scopus 로고
    • Reductive Rearrangement of Flavone Using Sodium Bis(2-methoxyethoxy)aluminum Dihydride
    • Katagi, T.; Aoki, M.; Katsu, S.; Kataoka, H.; Hanawa, T. Reductive Rearrangement of Flavone Using Sodium Bis(2-methoxyethoxy)aluminum Dihydride. Chem. Pharm. Bull. 1990, 38, 2256-2258.
    • (1990) Chem. Pharm. Bull. , vol.38 , pp. 2256-2258
    • Katagi, T.1    Aoki, M.2    Katsu, S.3    Kataoka, H.4    Hanawa, T.5
  • 15
    • 0000074391 scopus 로고
    • Reduction of Oxindoles with Sodium Bis(2-methoxyethoxy)aluminum Hydroxide: A Novel Reducing Agent
    • Pei, X. F.; Bi, S. Reduction of Oxindoles with Sodium Bis(2-methoxyethoxy)aluminum Hydroxide: a Novel Reducing Agent. Heterocycles 1994, 39, 357-360.
    • (1994) Heterocycles , vol.39 , pp. 357-360
    • Pei, X.F.1    Bi, S.2
  • 16
    • 0000609127 scopus 로고    scopus 로고
    • Practical Total Synthesis of Physostigmine and of Phenserine: A Synopsis
    • Pei, X. F.; Yu, Q. S.; Lu, B. Y.; Greig, N. H.; Brossi, A. Practical Total Synthesis of Physostigmine and of Phenserine: A Synopsis. Heterocycles 1996, 42, 229-236.
    • (1996) Heterocycles , vol.42 , pp. 229-236
    • Pei, X.F.1    Yu, Q.S.2    Lu, B.Y.3    Greig, N.H.4    Brossi, A.5
  • 17
    • 0002126741 scopus 로고
    • The Protonation of Tryptamine Derivatives in Acidic Media
    • Jackson, A. H.; Smith, A. E. The Protonation of Tryptamine Derivatives in Acidic Media. J. Chem. Soc. 1964, Suppl. 1, 5510.
    • (1964) J. Chem. Soc. , Issue.1 SUPPL. , pp. 5510
    • Jackson, A.H.1    Smith, A.E.2
  • 19
    • 0025975213 scopus 로고
    • Correlation between Plasma Physostigmine Concentration and Percentage of Acetylcholinesterase Inhibition over Time after Controlled-Release Physostigmine in Volunteer Subjects
    • Knapp, S.; Wardlow, M. L.; Albert, K.; Wasters, D.; Thal, L. J. Correlation between Plasma Physostigmine Concentration and Percentage of Acetylcholinesterase Inhibition over Time after Controlled-Release Physostigmine in Volunteer Subjects. Drug Metab. Dispos. 1990, 19, 400-404.
    • (1990) Drug Metab. Dispos. , vol.19 , pp. 400-404
    • Knapp, S.1    Wardlow, M.L.2    Albert, K.3    Wasters, D.4    Thal, L.J.5
  • 20
    • 0000549714 scopus 로고
    • Phenylcarbamates of (-)-Eseroline, (-)-N1-Noreseroline and (-)-Physovenol: Selective Inhibitors of Acetyl and, or Butrylcholinesterase
    • Brzostowska, M.; He, X. S.; Greig, N. H.; Brossi, A. Phenylcarbamates of (-)-Eseroline, (-)-N1-Noreseroline and (-)-Physovenol: Selective Inhibitors of Acetyl and, or Butrylcholinesterase. Med. Chem. Res. 1992, 2, 238-246.
    • (1992) Med. Chem. Res. , vol.2 , pp. 238-246
    • Brzostowska, M.1    He, X.S.2    Greig, N.H.3    Brossi, A.4
  • 21
    • 0001377977 scopus 로고
    • Thiaphysovenine and Carbamate Analogues: A New Class of Potent Inhibitors of Cholinesterases
    • He, X. S.; Greig, N. H.; Brossi, A.; Li, Y. Q.; Yu, Q. S. Thiaphysovenine and Carbamate Analogues: a New Class of Potent Inhibitors of Cholinesterases. Med. Chem. Res. 1992, 2, 227-237.
    • (1992) Med. Chem. Res. , vol.2 , pp. 227-237
    • He, X.S.1    Greig, N.H.2    Brossi, A.3    Li, Y.Q.4    Yu, Q.S.5
  • 22
    • 0000498371 scopus 로고
    • Preparation and Selective Inhibition of Human Butyrylcholinesterase by N1-Phenylethylnorphysostigmine analogues
    • Pei, X. F.; Greig, N. H.; Brossi, A. Preparation and Selective Inhibition of Human Butyrylcholinesterase by N1-Phenylethylnorphysostigmine analogues. Med. Chem. Res. 1995, 5, 455-461.
    • (1995) Med. Chem. Res. , vol.5 , pp. 455-461
    • Pei, X.F.1    Greig, N.H.2    Brossi, A.3
  • 23
    • 0024352019 scopus 로고
    • Comparison of Butyrylcholinesterase and Acetylcholinesterase
    • Chatonnet, A.; Lockridge, O. Comparison of Butyrylcholinesterase and Acetylcholinesterase. Biochem. J. 1989, 260, 625-634.
    • (1989) Biochem. J. , vol.260 , pp. 625-634
    • Chatonnet, A.1    Lockridge, O.2
  • 26
    • 15444346663 scopus 로고    scopus 로고
    • note
    • HPLC Chiracel OD column (25 cm × 0.4 cm i.d.; V(0) = 2.497 mL). Bases 6, 7, and 8 were dissolved in ether. Sample inject, 0.1 s; eluent, i-PrOH/hex = 10/90; flow rate, 1.0 mL/min; back pressure, 0.17 kpsi; detector, 254 nm.
  • 27
    • 0009767720 scopus 로고
    • Manske, K. H. F., Holmes, H. L., Eds.; Academic Press: New York
    • Robinson, R. In The Alkaloids; Manske, K. H. F., Holmes, H. L., Eds.; Academic Press: New York, 1967; Vol. 10, pp 383-401.
    • (1967) The Alkaloids , vol.10 , pp. 383-401
    • Robinson, R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.