Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 15, 2010, Pages 5576-5592

  Lawrence, Harshani R ^a   Kazi, Aslamuzzaman ^a   Luo, Yunting ^a   Kendig, Robert ^a   Ge, Yiyu ^a   Jain, Sanjula ^a   Daniel, Kenyon ^a   Santiago, Daniel ^c   Guida, Wayne C ^a,b,c   Sebti, Saïd M ^a,b  

^a H LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

^c UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

5 and 6 subunits; Chymotrypsin like (CT L); Naphthoquinone pharmacophore; Proteasome activity; Structure activity relationship (SAR)

Indexed keywords

2 CHLORO 3 (3 (ETHYLAMINOPEROXYTHIO)PHENYLAMINO)NAPHTHALENE 1,4 DIONE; 2 CHLORO 3 (3 (ISOPROPYLAMINOPEROXYTHIO)PHENYLAMINO)NAPHTHALENE 1,4 DIONE; 2 CHLORO 3 (3 (METHYLAMINOPEROXYTHIO)PHENYLAMINO)NAPHTHALENE 1,4 DIONE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) 2 METHOXY N (4 METHOXYPHENYL) BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) 2 METHOXY N 2 TOLYL BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) 2 METHOXY N 3 TOLYL BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) 2 METHOXY N 4 TOLYL BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) N (2 METHOXYPHENYL) BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) N (3 METHOXYPHENYL) BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) N (4 METHOXYPHENYL) BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) N 2 TOLYL BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) N 3 TOLYLBENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) N 4 TOLYLBENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRO NAPHTHALEN 2 YLAMINO) N PHENYLBENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLAMINO) N (1 PHENYL 1H PYRAZOL 4 YL)BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLAMINO) N (3,4 DIMETHYLISOXAZOL YL)BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLAMINO) N (4,6 DIMETHYLPYRINIDIN 2 YL)BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLAMINO) N (5 METHYL 1,3,4 THIADIAZOL 2 YL)BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLAMINO) N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLAMINO) N (THIAZOL 2 YLL)BENZENE SULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLAMINO) N ETHYLBENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLAMINO) N ISOPROPYLBENZENESULFONAMIDE; 4 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLAMINO) N METHYLBENZENESULFONAMIDE; ANTINEOPLASTIC AGENT; BORTEZOMIB; CHLORONAPHTHOQUINONE; NAPHTHOXAZINE DERIVATIVE; NSC 45382; PI 083; PROTEASOME INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTHRACYCLINE; NAPHTHOQUINONE; PROTEASOME; PROTEIN SUBUNIT; PROTEINASE INHIBITOR; SULFONAMIDE;

ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; HYDROGEN BOND; IC 50; IN VITRO STUDY; MOUSE; MULTIPLE MYELOMA; NONHUMAN; STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMISTRY; COMPUTER SIMULATION; METABOLISM; PROTEIN SUBUNIT; SYNTHESIS;

ANTHRACYCLINES; BINDING SITES; COMPUTER SIMULATION; HYDROGEN BONDING; NAPHTHOQUINONES; PROTEASE INHIBITORS; PROTEASOME ENDOPEPTIDASE COMPLEX; PROTEIN SUBUNITS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; PROTEASOME INHIBITORS;

EID: 77955420821     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.06.038     Document Type: Article

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