Phenylthio-derivatives of α-methylene-γ-lactones as pro-drugs of cytotoxic agents

…, P Barbetti, G Grandolini, I Chiappini, V Ambrogi…

Index: Fardella, Giuseppe; Barbetti, Paolo; Grandolini, Giuliano; Chiappini, Ione; Ambrogi, Valeria; Scarcia, Vito; Furlani Candiani, Ariella European Journal of Medicinal Chemistry, 1999 , vol. 34, # 6 p. 515 - 523

Full Text: HTML

Citation Number: 19

Abstract

A series of substituted phenylthio-derivatives of grosheimin (1), a natural cytotoxic guaianolide, were investigated with the aim of providing insight into their mechanism of action as cytotoxic agents against KB cell lines. Hydrolysis data, kinetics, in the presence and in the absence of H2O2, and the valuation of lipophilicity were correlated with cytotoxicity values and with Hammett-σ-values of substituents (R) at the thiophenol ring. ...

 Related Synthetic Route
(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-3-(((2-methoxyphenyl)thio)methyl)-9-methyl-6-methyleneoctahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-44-3

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

1-THIAZOL-2-YL-ETHANOL Structure

34256-00-3

1-THIAZOL-2-YL-...

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylene-3-((phenylthio)methyl)octahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-40-9

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

Thiophenol Structure

108-98-5

Thiophenol

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylene-3-((phenylthio)methyl)octahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-40-9

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

Benzenesulfonic acid Structure

98-11-3

Benzenesulfonic acid

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylene-3-((m-tolylthio)methyl)octahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-38-5

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

4-Methylthiophenol Structure

108-40-7

4-Methylthiophenol

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylene-3-((m-tolylthio)methyl)octahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-38-5

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

3,4-DICHLORO-BENZENESULFONIC ACID Structure

617-97-0

3,4-DICHLORO-BE...

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-3-(((4-methoxyphenyl)thio)methyl)-9-methyl-6-methyleneoctahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-42-1

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

4-Methoxythiophenol Structure

696-63-9

4-Methoxythiophenol

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-3-(((4-methoxyphenyl)thio)methyl)-9-methyl-6-methyleneoctahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-42-1

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

3-CHLORO-PYRROLIDINE Structure

5857-42-1

3-CHLORO-PYRROLIDINE

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-3-(((2-methoxyphenyl)thio)methyl)-9-methyl-6-methyleneoctahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-44-3

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

2-Methoxybenzenethiol Structure

7217-59-6

2-Methoxybenzen...

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-3-(((2-methoxyphenyl)thio)methyl)-9-methyl-6-methyleneoctahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-44-3

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

1-THIAZOL-2-YL-ETHANOL Structure

34256-00-3

1-THIAZOL-2-YL-...

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-3-(((3-methoxyphenyl)thio)methyl)-9-methyl-6-methyleneoctahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-43-2

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

4-Methoxythiophenol Structure

15570-12-4

4-Methoxythiophenol

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-3-(((3-methoxyphenyl)thio)methyl)-9-methyl-6-methyleneoctahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-43-2

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

2-(1-CHLORO-ETHYL)-THIAZOLE Structure

34256-01-4

2-(1-CHLORO-ETH...

N/A Structure

248584-39-6

N/A

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

2-Toluenesulfonic acid Structure

88-20-0

2-Toluenesulfon...

N/A Structure

248584-39-6

N/A

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

o-Thiocresol Structure

137-06-4

o-Thiocresol

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylene-3-((p-tolylthio)methyl)octahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-37-4

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

p-Toluenesulfonic acid Structure

104-15-4

p-Toluenesulfon...

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylene-3-((p-tolylthio)methyl)octahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-37-4

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

P-toluenethiol Structure

106-45-6

P-toluenethiol

N-(4-((((3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylene-2,8-dioxododecahydroazuleno[4,5-b]furan-3-yl)methyl)thio)phenyl)acetamide Structure

248584-41-0

N-(4-((((3S,3aR...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

4-Acetamidobenzenesulfonic Acid Structure

121-62-0

4-Acetamidobenz...

N-(4-((((3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylene-2,8-dioxododecahydroazuleno[4,5-b]furan-3-yl)methyl)thio)phenyl)acetamide Structure

248584-41-0

N-(4-((((3S,3aR...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

4-acetamidothiophenol Structure

1126-81-4

4-acetamidothio...

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-3-(((3-methoxyphenyl)thio)methyl)-9-methyl-6-methyleneoctahydroazuleno[4,5-b]furan-2,8(3H,9bH)-dione Structure

248584-43-2

(3S,3aR,4S,6aR,...

~%

Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)- Structure

22489-66-3

Azuleno[4,5-b]f...

2-(1-CHLORO-ETHYL)-THIAZOLE Structure

34256-01-4

2-(1-CHLORO-ETH...


Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved