Synthesis, structure-activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 24, 2011, Pages 7541-7550

  Kamiyama, Haruka ^a   Kubo, Yoshinao ^a   Sato, Hironori ^a,b   Yamamoto, Naoki ^a,c   Fukuda, Tsutomu ^a   Ishibashi, Fumito ^a   Iwao, Masatomo ^a  

^a NAGASAKI UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF INFECTIOUS DISEASES   (Japan)

^c NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Anti HIV 1 activity; Entry inhibiting activity; Lamellarin sulfates; Structure activity relationships

Indexed keywords

14 (3 HYDROXY 4 METHOXYPHENYL) 2,11,12 TRIMETHOXY 6 OXO 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 3 YL 2,2,2 TRICHLOROETHYL SULFATE; 2,2,2 TRICHLOROETHYL 2,11,12 TRIMETHOXY 14 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] 6 OXO 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 3 YL SULFATE; 3 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 3,4 DIHYDRO 1 (3 HYDROXY 4 METHOXYPHENYL) 8 METHOXY 4 OXO [1]BENZOPYRANO[3,4 B]PYRROL 7 YL 2,2,2 TRICHLOROETHYL SULFATE; 3 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 3,4 DIHYDRO 8 METHOXY 1 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] 4 OXO [1]BENZOPYRANO[3,4 B]PYRROL 7 YL 2,2,2 TRICHLOROETHYL SULFATE; 3 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 7 HYDROXY 8 METHOXY 1 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] [1]BENZOPYRANO[3,4 B]PYRROL 4(3H) ONE; 3 BENZYLOXY 14 (3 HYDROXY 4 METHOXYPHENYL) 2,11,12 TRIMETHOXY 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 6 ONE; 3 BENZYLOXY 2,11,12 TRIMETHOXY 14 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 6 ONE; 3 BENZYLOXY 8,9 DIHYDRO 2,11,12 TRIMETHOXY 14 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 6 ONE; 3 HYDROXY 14 (3 HYDROXY 4 METHOXYPHENYL) 2,11,12 TRIMETHOXY 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 6 ONE; 3 HYDROXY 2,11,12 TRIMETHOXY 14 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 6 ONE; 5 [3 BENZYLOXY 2,11,12 TRIMETHOXY 6 OXO 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 14 YL] 2 METHOXYPHENYL 2,2,2 TRICHLOROETHYL SULFATE; 5 [3 HYDROXY 2,11,12 TRIMETHOXY 6 OXO 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 14 YL] 2 METHOXYPHENYL 2,2,2 TRICHLOROETHYL SULFATE; 7 BENZYLOXY 3 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 3,4 DIHYDRO 8 METHOXY 1 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] 4 OXO [1]BENZOPYRANO[3,4 B]PYRROLE 2 CARBOXYLATE; 7 BENZYLOXY 3 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 8 METHOXY 1 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] 4 OXO [1]BENZOPYRANO[3,4 B]PYRROLE 2 CARBOXYLATE; 7 BENZYLOXY 3 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 8 METHOXY 1 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] [1]BENZOPYRANO[3,4 B]PYRROL 4(3H) ONE; 8,9 DIHYDRO 14 (3 HYDROXY 4 METHOXYPHENYL) 2,11,12 TRIMETHOXY 6 OXO 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 3 YL SULFATE; 8,9 DIHYDRO 14 (3 HYDROXY 4 METHOXYPHENYL) 2,11,12 TRIMETHOXY 6 OXO 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 3YL 2,2,2 TRICHLOROETHYL SULFATE; 8,9 DIHYDRO 2,11,12 TRIMETHOXY 14 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] 6 OXO 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 3YL 2,2,2 TRICHLOROETHYL SULFATE; 8,9 DIHYDRO 3 HYDROXY 2,11,12 TRIMETHOXY 14 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 6 ONE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DIMETHYL 3 [4 BENZYLOXY 5 METHOXY 2 (METHOXYMETHOXY)PHENYL] 1 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 4 (TRIFLUOROMETHANESULFONYLOXY)PYRROLE 2,5 DICARBOXYLATE; LAMELLARIN ALPHA 20 SULFATE DERIVATIVE; METHYL 7 BENZYLOXY 3 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 3,4 DIHYDRO 8 METHOXY 1 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL] 4 OXO [1]BENZOPYRANO[3,4 B]PYRROLE 2 CARBOXYLATE; METHYL 7 BENZYLOXY 3 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 3,4 DIHYDRO 8 METHOXY 4 OXO 1 (TRIFLUOROMETHANESULFONYLOXY) [1]BENZOPYRANO[3,4 B]PYRROLE 2 CARBOXYLATE; SODIUM 14 (3 HYDROXY 4 METHOXYPHENYL) 2,11,12 TRIMETHOXY 6 OXO 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 3 YL SULFATE; SODIUM 3 [2 (3,4 DIMETHOXYPHENYL)ETHYL] 3,4 DIHYDRO 1 (3 HYDROXY 4 METHOXYPHENYL) 8 METHOXY 4 OXO [1]BENZOPYRANO[3,4 B]PYRROL 7 YL 2,2,2 TRICHLOROETHYL SULFATE; SODIUM 5 [3 HYDROXY 2,11,12 TRIMETHOXY 6 OXO 6H [1]BENZOPYRANO[4',3':4,5]PYRROLO[2,1 A]ISOQUINOLIN 14 YL] 2 METHOXYPHENYL SULFATE; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HELA CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 1 INFECTION; IC 50; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; CELL LINE; COUMARINS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HIV INFECTIONS; HIV INTEGRASE INHIBITORS; HIV-1; HUMANS; ISOQUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 82255179034     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.10.030     Document Type: Article

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