메뉴 건너뛰기




Volumn 55, Issue 23, 1999, Pages 7221-7232

Solid-phase synthesis of hydroxamic acid based TNF-α convertase inhibitors

Author keywords

Acylation; Hydroxamic acid; Reductive amination; Solid phase synthesis

Indexed keywords

HYDROXAMIC ACID; RESIN; SASRIN; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

EID: 0033523078     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00347-6     Document Type: Article
Times cited : (34)

References (28)
  • 1
    • 0013626659 scopus 로고    scopus 로고
    • note
    • This work was presented in part at the "Journées de Chimie Organique" meeting (September 15-17, 1998, Palaiseau, France), abstract n° A 153
  • 6
    • 8044257704 scopus 로고    scopus 로고
    • Isolation of TACE: a) Black, R.A. and al. Nature 1997, 385, 729
    • (1997) Nature , vol.385 , pp. 729
    • Black, R.A.1
  • 7
    • 8044250278 scopus 로고    scopus 로고
    • b) Moos, M.L. and al. Nature 1997, 385, 733
    • (1997) Nature , vol.385 , pp. 733
    • Moos, M.L.1
  • 8
    • 0030605136 scopus 로고    scopus 로고
    • During the course of this work, resin 1 was mentioned briefly by Richter (ref. 5b) and Gordeev (ref 5i). For recent papers on solid phase synthesis of hydroxamic acids: a) Floyd, C.; Lewis, C.; Patel, S.R.; Whittaker, M. Tetrahedron Lett. 1996, 37, 8045
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8045
    • Floyd, C.1    Lewis, C.2    Patel, S.R.3    Whittaker, M.4
  • 14
    • 0013604411 scopus 로고    scopus 로고
    • PCT Int. Appl. WO97/24117 (Rhone-Poulenc Rorer)
    • g) McGeehan, G.M et al. PCT Int. Appl. WO97/24117 (Rhone-Poulenc Rorer); Chem. Abst. 127:161589
    • Chem. Abst. , vol.127 , pp. 161589
    • McGeehan, G.M.1
  • 19
    • 0013607277 scopus 로고    scopus 로고
    • note
    • H1,H2 = 5.9 Hz).
  • 20
    • 0013577014 scopus 로고    scopus 로고
    • note
    • Loading of resin 3 may vary from batch to batch. Yields have been calculated with loading of resin 3 set to 0.5 mmol/g. Compounds 2a-c have been isolated without further purification; they may contain traces of solvents and/or minor impurities. All these factors may explain that yields were found greater than 100% in some cases.
  • 23
    • 84987276692 scopus 로고
    • Harmon has previously shown that reaction of α-amino hydroxamic acids with aldehydes gave the corresponding imidazolinones: Harmon, R.E.; Rizzo, V.L.; Gupta, S.K. J. Heterocycl. Chem. 1970, 7, 439
    • (1970) J. Heterocycl. Chem. , vol.7 , pp. 439
    • Harmon, R.E.1    Rizzo, V.L.2    Gupta, S.K.3
  • 24
    • 0013575112 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 9807742 (Zeneca); Biological activities of these MMP/TACE inhibitors will be reported elsewhere in due course
    • a) Barlaam, B PCT Int. Appl. WO 9807742 (Zeneca); Chem. Abst. 128:205148. Biological activities of these MMP/TACE inhibitors will be reported elsewhere in due course;
    • Chem. Abst. , vol.128 , pp. 205148
    • Barlaam, B.1
  • 25
    • 4243299851 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 9749674 (Pharmacia-Upjohn); In this patent, Alpegiani et al. reported a adduct similar to 17 with acetone
    • b) For the synthesis of similar compounds in solution, see: Alpegiani, M.; Abrate, F.; Bissolino, P.; Palladino, M.; Perrone, E. PCT Int. Appl. WO 9749674 (Pharmacia-Upjohn); Chem. Abst. 128:089110. In this patent, Alpegiani et al. reported a adduct similar to 17 with acetone.
    • Chem. Abst. , vol.128 , pp. 089110
    • Alpegiani, M.1    Abrate, F.2    Bissolino, P.3    Palladino, M.4    Perrone, E.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.