메뉴 건너뛰기




Volumn 46, Issue 18, 2003, Pages 3840-3852

Stereospecific synthesis of 5-substituted 2-bisarylthiocyclopentane carboxylic acids as specific matrix metalloproteinase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

2 [2 (4' CHLOROBIPHENYL)ETHYLSULFONYL] 5 (PHTHALIMIDOMETHYL)CYCLOPENTANECARBOXYLIC ACID; 2 [2 (4' CHLOROBIPHENYL)ETHYLTHIO] 5 (PHTHALIMIDOMETHYL)CYCLOPENTANECARBOXYLIC ACID; 2 [2 (4' CHLOROBIPHENYL)ETHYLTHIO] 5 [2 (4 OXO 4H BENZO[D][1,2,3]TRIAZIN 3 YLMETHYL)]CYCLOPENTANECARBOXYLIC ACID; 2 [2 (4' CHLOROBIPHENYLTHIO)] 5 [2 (4 OXO 4H BENZO[D][1,2,3]TRIAZIN 3 YL METHYL)]CYCLOPENTANECARBOXYLIC ACID; 2 [2 (4' FLUOROBIPHENYL)ETHYLTHIO] 5 (PHTHALIMIDOMETHYL)CYCLOPENTANECARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; CGS 27023A; CIPEMASTAT; COLLAGENASE 3; CYCLOPENTANE DERIVATIVE; GELATINASE A; GELATINASE B; INTERSTITIAL COLLAGENASE; MARIMASTAT; MATRIX METALLOPROTEINASE; MATRIX METALLOPROTEINASE INHIBITOR; PRINOMASTAT; STROMELYSIN; UNCLASSIFIED DRUG;

EID: 0042929694     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0307638     Document Type: Article
Times cited : (31)

References (43)
  • 1
    • 0033618337 scopus 로고    scopus 로고
    • Matrix mettaloproteinases
    • (a) Nagase, H.; Woessner, J. F., Jr. Matrix Mettaloproteinases. J. Biol. Chem. 1999, 274, 21491-21494,
    • (1999) J. Biol. Chem. , vol.274 , pp. 21491-21494
    • Nagase, H.1    Woessner J.F., Jr.2
  • 4
    • 0031929152 scopus 로고    scopus 로고
    • Development of osteoarthritis in the knee joints of wistar rats after strenuous running exercise in a running wheel by intracranial self-stimulation
    • (b) Pap, G.; Eberhardt, R.; Stürmer, I.; Machner, A.; Schwarzberg, H.; Roessner, A.; Neumann, W. Development of Osteoarthritis in the Knee Joints of Wistar Rats After Strenuous Running Exercise in a Running Wheel by Intracranial Self-Stimulation. Pathol. Res. Practice 1998,194, 41-47.
    • (1998) Pathol. Res. Practice , vol.194 , pp. 41-47
    • Pap, G.1    Eberhardt, R.2    Stürmer, I.3    Machner, A.4    Schwarzberg, H.5    Roessner, A.6    Neumann, W.7
  • 5
    • 0029833035 scopus 로고    scopus 로고
    • Cytokine control of interstitial collagenase and collagenase-3 gene expression in human chondrocytes
    • (c) Borden, P.; Solymar, D.; Sucharczuk, A.; Lindman, B.; Cannon, P.; Heller, R. A. Cytokine Control of Interstitial Collagenase and Collagenase-3 Gene Expression in Human Chondrocytes. J. Biol. Chem. 1996, 271, 23577-23581.
    • (1996) J. Biol. Chem. , vol.271 , pp. 23577-23581
    • Borden, P.1    Solymar, D.2    Sucharczuk, A.3    Lindman, B.4    Cannon, P.5    Heller, R.A.6
  • 6
    • 0036512208 scopus 로고    scopus 로고
    • New functions for the matrix metalloproteases in cancer progression
    • (a) Egeblad, M.; Werb, Z. New Functions for the Matrix Metalloproteases in Cancer Progression. Nat. Rev. 2002, 2, 161-174.
    • (2002) Nat. Rev. , vol.2 , pp. 161-174
    • Egeblad, M.1    Werb, Z.2
  • 7
    • 0000276686 scopus 로고    scopus 로고
    • Matrix metallproteinase inhibitors in cancer: An update
    • (b) Marshall, J. L.; Baidas, S.; Bhargava, P.; Rizvi, N. Matrix Metallproteinase Inhibitors in Cancer: An Update. IDrugs 2000, 3, 5, 518-524.
    • (2000) IDrugs , vol.3 , pp. 518-524
    • Marshall, J.L.1    Baidas, S.2    Bhargava, P.3    Rizvi, N.4
  • 8
    • 0032520784 scopus 로고    scopus 로고
    • Bi-directional induction of matrix metallproteinase-9 and tissue inhibitor of matrix metallproteinase-1 during T lymphoma/endothetial cell contact: Implication of ICAM-1
    • (c) Aoudjit, F.; Potworowski, E. F.; St-Pierre, Y. Bi-Directional Induction of Matrix Metallproteinase-9 and Tissue Inhibitor of Matrix Metallproteinase-1 During T Lymphoma/Endothetial Cell Contact: Implication of ICAM-1. J. Immunol. 1998, 160, 2967-2973.
    • (1998) J. Immunol. , vol.160 , pp. 2967-2973
    • Aoudjit, F.1    Potworowski, E.F.2    St-Pierre, Y.3
  • 9
    • 0031969838 scopus 로고    scopus 로고
    • Influence of cytokines and growth factors on matrix metalloproteinase-2 production and invasion of human renal cancer
    • (d) Gohji, K.; Nomi, M.; Hara, I.; Arakawa, S.; Kamidono, S. Influence of Cytokines and Growth factors on matrix metalloproteinase-2 production and invasion of human renal cancer. Urol. Res. 1998, 1, 33-37.
    • (1998) Urol. Res. , vol.1 , pp. 33-37
    • Gohji, K.1    Nomi, M.2    Hara, I.3    Arakawa, S.4    Kamidono, S.5
  • 14
    • 0033946952 scopus 로고    scopus 로고
    • Metalloproteinase inhibitors: New opportunities for the treatment of rheumatoid arthritis and osteoarthritis
    • (c) Shaw, T.; Nixon, J. S.; Bottomley, K. M. Metalloproteinase inhibitors: new opportunities for the treatment of rheumatoid arthritis and osteoarthritis. Exp. Opin. Invest. Drugs 2000, 9, 7, 1469-1478.
    • (2000) Exp. Opin. Invest. Drugs , vol.9 , pp. 1469-1478
    • Shaw, T.1    Nixon, J.S.2    Bottomley, K.M.3
  • 15
    • 0030839472 scopus 로고    scopus 로고
    • Matrix metalloproteinase inhibition as a novel anticancer strategy: A review with special focus on batimastat and marimastat
    • Rasmussen, H. S.; McCann, P. P. Matrix Metalloproteinase Inhibition as a Novel Anticancer Strategy: A Review with Special Focus on Batimastat and Marimastat. Pharmacol. Ther. 1997, 75, 1, 69-75.
    • (1997) Pharmacol. Ther. , vol.75 , pp. 69-75
    • Rasmussen, H.S.1    McCann, P.P.2
  • 16
    • 0030816454 scopus 로고    scopus 로고
    • Rodent pharmacokinetic and antitumor efficacy studies with a series of synthetic inhibitors of matrix metalloproteinases
    • (a) Santos, O.; Mcdermott, C. D.; Daniels, R. G.; Appelt, K. Rodent pharmacokinetic and antitumor efficacy studies with a series of synthetic inhibitors of matrix metalloproteinases. Clin. Exp. Metastasis 1997, 15, 499-508.
    • (1997) Clin. Exp. Metastasis , vol.15 , pp. 499-508
    • Santos, O.1    Mcdermott, C.D.2    Daniels, R.G.3    Appelt, K.4
  • 17
    • 0032449008 scopus 로고    scopus 로고
    • Antitumor efficacy of AG3340 associated with maintenance of minimum effective plasma concentrations and not total daily dose, exposure or peak plasma concentrations
    • (b) Shalinsky, D. R.; Brekken, J.; Zou, H.; Kolis, S.; Wood, A.; Webber, S.; Appelt, K. Antitumor efficacy of AG3340 associated with maintenance of minimum effective plasma concentrations and not total daily dose, exposure or peak plasma concentrations. Invest. New Drug 1999, 16, 303-313.
    • (1999) Invest. New Drug , vol.16 , pp. 303-313
    • Shalinsky, D.R.1    Brekken, J.2    Zou, H.3    Kolis, S.4    Wood, A.5    Webber, S.6    Appelt, K.7
  • 20
    • 0042675988 scopus 로고    scopus 로고
    • RS-130830, a selective inhibitor of collagenase-3 blocks the release of hydroxyproline and a metalloproteinase specific neoepitope, COLL II CTx, from bovine cartilage exposed to IL-1α
    • Abst 584
    • Atley, L.; DeLustro, B.; Eugui, E.; Martin, R.; Eyre, D.; Caulfield, J. P. RS-130830, a selective inhibitor of collagenase-3 blocks the release of hydroxyproline and a metalloproteinase specific neoepitope, COLL II CTx, from bovine cartilage exposed to IL-1α. Arthritis Rheum. 1997, 40, (9, Suppl.): Abst 584.
    • (1997) Arthritis Rheum. , vol.40 , Issue.9 SUPPL.
    • Atley, L.1    DeLustro, B.2    Eugui, E.3    Martin, R.4    Eyre, D.5    Caulfield, J.P.6
  • 27
    • 0000562947 scopus 로고
    • Preparation and reactions of dialkoxytetrahydrofurans
    • Fakstorp, J.; Raleigh, D.; Schniepp, L. E. Preparation and Reactions of Dialkoxytetrahydrofurans. J. Am. Chem. Soc. 1950, 72, 869-874.
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 869-874
    • Fakstorp, J.1    Raleigh, D.2    Schniepp, L.E.3
  • 28
    • 0000148163 scopus 로고
    • La réaction de Wittig-Horner en milieu hétérogène IX. Bis aldolisation des phosphanates à partir des dialdéhydes aliphatiques en milieu aqueux peu basique. Synthèse de cyclenols fonctionnels
    • (a) Graff, M.; Al Dilaimi, A.; Seguineau, P.; Rambaud, M.; Villiéras, J. La réaction de Wittig-Horner en milieu hétérogène IX. Bis aldolisation des phosphanates à partir des dialdéhydes aliphatiques en milieu aqueux peu basique. Synthèse de cyclenols fonctionnels. Tetrahedron Lett. 1986, 27, 14, 1577-1578.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1577-1578
    • Graff, M.1    Al Dilaimi, A.2    Seguineau, P.3    Rambaud, M.4    Villiéras, J.5
  • 29
    • 0002559860 scopus 로고
    • The Wittig-Horner reaction in heterogeneous media VIII. Cyclisation during the aldolisation step from aqueous glutaraldehyde
    • (b) Villiéras, J.; Rambaud, M.; Graff, M. The Wittig-Horner reaction in heterogeneous media VIII. Cyclisation during the aldolisation step from aqueous glutaraldehyde. Synth. Commun. 1986, 16, 2, 149-156.
    • (1986) Synth. Commun. , vol.16 , pp. 149-156
    • Villiéras, J.1    Rambaud, M.2    Graff, M.3
  • 30
    • 0042174795 scopus 로고
    • 1,4-Addition of lithiated derivatives from 1,3-dithianes to α-unsaturated aldehydes: A way to δ-carbonyl aldehydes
    • El-Bouz, M.; Wartski, L. 1,4-addition of lithiated derivatives from 1,3-dithianes to α-unsaturated aldehydes: a way to δ-carbonyl aldehydes. Tetrahedron Lett. 1980, 21, 2897-2900.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 2897-2900
    • El-Bouz, M.1    Wartski, L.2
  • 32
    • 0030603075 scopus 로고    scopus 로고
    • Copper(I) mediated highly diastereoselective conjugate addition of grignard reagents to 2-silyloxy cyclopentenecarboxylates
    • Dambrin, V.; Villiéras, M.; Moreau, C.; Amri, H.; Loupet, L.; Villiéras, J. Copper(I) mediated Highly Diastereoselective Conjugate Addition of Grignard Reagents to 2-Silyloxy cyclopentenecarboxylates. Tetrahedron Lett. 1996, 37, 35, 6323-6326.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6323-6326
    • Dambrin, V.1    Villiéras, M.2    Moreau, C.3    Amri, H.4    Loupet, L.5    Villiéras, J.6
  • 35
    • 0002667764 scopus 로고
    • The mistunobu reaction
    • Mitsunobu, O. The Mistunobu Reaction. Synthesis 1981, 1-28.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 36
    • 0001651169 scopus 로고    scopus 로고
    • Design and therapeutic appplication of matrix metalloproteinase inhibitors
    • and references cited herein
    • Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Design and therapeutic appplication of matrix metalloproteinase inhibitors. Chem. Rev. 1999, 99, 2735-2776 and references cited herein.
    • (1999) Chem. Rev. , vol.99 , pp. 2735-2776
    • Whittaker, M.1    Floyd, C.D.2    Brown, P.3    Gearing, A.J.H.4
  • 37
    • 0003094064 scopus 로고    scopus 로고
    • Structural insights into the catalytic domains o human matrix metalloprotease-2 and human matrix metalloprotease-9 implications for substrate specificities
    • and references cited herein
    • Massova, I.; Fridman, R.; Mobashery, S. Structural Insights into the Catalytic Domains o Human Matrix Metalloprotease-2 and Human Matrix Metalloprotease-9 Implications for Substrate Specificities. J. Mol. Model. 1997, 1, 3, 17-30 and references cited herein.
    • (1997) J. Mol. Model. , vol.1 , Issue.3 , pp. 17-30
    • Massova, I.1    Fridman, R.2    Mobashery, S.3
  • 38
    • 0042675986 scopus 로고    scopus 로고
    • SYBYL 6.8, Tripos Inc., 1699 South Hanley Road, Saint-Louis, MO 63144, USA, running on an Octane R12000 Silicon Graphics workstation
    • SYBYL 6.8, Tripos Inc., 1699 South Hanley Road, Saint-Louis, MO 63144, USA, running on an Octane R12000 Silicon Graphics workstation.
  • 39
    • 5544242529 scopus 로고    scopus 로고
    • MMFF VI. MMFF94s option for energy minimization studies
    • Halgren, T. A. MMFF VI. MMFF94s option for energy minimization studies. J. Comput. Chem. 1999, 20(7), 720.
    • (1999) J. Comput. Chem. , vol.20 , Issue.7 , pp. 720
    • Halgren, T.A.1
  • 40
    • 0028140295 scopus 로고
    • Suppression of the tumorigenic and metastatic abilities of murine B16-F10 melanoma cells in vivo by the overextression of the tissue inhibitor of the metalloproteinases-1
    • Khokha, R. Suppression of the Tumorigenic and Metastatic Abilities of Murine B16-F10 Melanoma Cells In Vivo by the Overextression of the Tissue Inhibitor of the Metalloproteinases-1. J. Natl. Cancer Inst. 1994, 86, 4, 299-304.
    • (1994) J. Natl. Cancer Inst. , vol.86 , pp. 299-304
    • Khokha, R.1
  • 41
    • 0028145441 scopus 로고
    • Design and characterization of a fluorogenic substrate selectively hydrolyzed by stromelysin 1 (matrix metalloproteinase-3)
    • Nagase, H.; Fields, C. G.; Fields, G. B. Design and Characterization of a Fluorogenic Substrate Selectively Hydrolyzed by Stromelysin 1 (Matrix Metalloproteinase-3). J. Biol. Chem. 1994, 269, 33, 20952-20957.
    • (1994) J. Biol. Chem. , vol.269 , pp. 20952-20957
    • Nagase, H.1    Fields, C.G.2    Fields, G.B.3
  • 43
    • 0017138981 scopus 로고
    • Brief communication: Organ selectivity for implantation survival and growth of B16 melanoma variant tumor lines
    • Fidler, I. J. and Nicolson, G. L. Brief Communication: Organ Selectivity for Implantation Survival and Growth of B16 Melanoma Variant Tumor Lines. J. Natl. Cancer Inst. 1976, 57, 5, 1199-1202.
    • (1976) J. Natl. Cancer Inst. , vol.57 , pp. 1199-1202
    • Fidler, I.J.1    Nicolson, G.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.