The sulfonimidamide as a novel transition state analog for aspartic acid and metallo proteases

被引：29

作者：

Cathers, BE ^{[1
]}

Schloss, JV ^{[1
]}

机构：

[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 11期

关键词：

D O I：

10.1016/S0960-894X(99)00241-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We have developed a novel strategy for the preparation of tetrahedral transition state analogs for aspartic acid and metallo-proteases based upon the sulfonimidamide functional group. Our best alpha-des-amino dipeptide analog binds at least 100-fold tighter than the corresponding ground state structure (i.e., amide). A previously unpublished five-membered cyclic sulfonimidamide was also synthesized. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1527 / 1532

页数：6

相关论文

共 25 条

[1] ALKYL AND ARYL SULFENIMIDES [J].

BEHFOROUZ, M ;

KERWOOD, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (01) :51-+

[2] PHOSPHORUS-CONTAINING INHIBITORS OF ENDOTHELIN CONVERTING ENZYME - EFFECTS OF THE ELECTRONIC NATURE OF PHOSPHORUS ON INHIBITOR POTENCY [J].

BERTENSHAW, SR ;

ROGERS, RS ;

STERN, MK ;

NORMAN, BH ;

MOORE, WM ;

JEROME, GM ;

BRANSON, LM ;

MCDONALD, JF ;

MCMAHON, EG ;

PALOMO, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (01) :173-176

[3] Phosphinic acid inhibitors of matrix metalloproteinases [J].

Caldwell, CG ;

Sahoo, SP ;

Polo, SA ;

Eversole, RR ;

Lanza, TJ ;

Mills, SG ;

Niedzwiecki, LM ;

IzquierdoMartin, M ;

Chang, BC ;

Harrison, RK ;

Kuo, DW ;

Lin, TY ;

Stein, RL ;

Durette, PL ;

Hagmann, WK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (03) :323-328

[4] Enzyme-coupled assays for proteases [J].

Cathers, BE ;

Schloss, JV .

ANALYTICAL BIOCHEMISTRY, 1996, 241 (01) :1-4

[5] CHEMISTRY OF SULFUR-NITROGEN BOND .12. METAL-ASSISTED SYNTHESIS OF SULFENAMIDE DERIVATIVES FROM ALIPHATIC AND AROMATIC DISULFIDES [J].

DAVIS, FA ;

FRIEDMAN, AJ ;

KLUGER, EW ;

SKIBO, EB ;

FRETZ, ER ;

MILICIA, AP ;

LEMASTERS, WC ;

BENTLEY, MD ;

LACADIE, JA ;

DOUGLASS, IB .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (06) :967-972

[6] L-735,524 - THE DESIGN OF A POTENT AND ORALLY BIOAVAILABLE HIV PROTEASE INHIBITOR [J].

DORSEY, BD ;

LEVIN, RB ;

MCDANIEL, SL ;

VACCA, JP ;

GUARE, JP ;

DARKE, PL ;

ZUGAY, JA ;

EMINI, EA ;

SCHLEIF, WA ;

QUINTERO, JC ;

LIN, JH ;

CHEN, IW ;

HOLLOWAY, MK ;

FITZGERALD, PMD ;

AXEL, MG ;

OSTOVIC, D ;

ANDERSON, PS ;

HUFF, JR .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (21) :3443-3451

[7] SYNTHESES OF AMINO ALKYL SULPHONIC ACIDS AND THEIR PEPTIDE ANALOGUES [J].

FRANKEL, M ;

MOSES, P .

TETRAHEDRON, 1960, 9 (3-4) :289-294

[8] SYNTHESIS OF CARBAMATES OF ALPHA-AMINO SULFONAMIDES [J].

GILMORE, WF ;

LIN, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (23) :4535-4537

[9] SELECTIVE PHOSPHINATE TRANSITION-STATE ANALOG INHIBITORS OF THE PROTEASE OF HUMAN-IMMUNODEFICIENCY-VIRUS [J].

GROBELNY, D ;

WONDRAK, EM ;

GALARDY, RE ;

OROSZLAN, S .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 169 (03) :1111-1116

[10] SYNTHESIS AND PROPERTIES OF N-(ALKYL-ARYLSULFINYL AND ARYLSULFINYL)PHTHALIMIDES - NEW CLASS OF SULFINYL-TRANSFER REAGENTS [J].

HARPP, DN ;

BACK, TG .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (25) :4328-4334