BIOMAT Database Logo BIOMAT Database Logo

Novel cyano- and N-isopropylamidino-substituted derivatives of benzo[b]thiophene-2-carboxanilides and benzo[b]thieno[2,3-c]quinolones: synthesis, photochemical synthesis, crystal structure determination, and antitumor evaluation. 2. 2005

Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, P.O. Box 177, HR-10000 Zagreb, Croatia.

Derivatives of 3-chlorobenzo[b]thiophene-2-carboxanilides and their "cyclic" analogues benzo[b]thieno[2,3-c]quinolones were synthesized. Spectroscopic study of the interactions of some representatives of "cyclic" derivatives and their "acyclic" precursors with ds-DNA/RNA supported strong intercalative binding of the former and weak nonintercalative binding of the latter group of compounds. All tested compounds showed a certain antiproliferative effect on a series of human tumor cells and on a normal cell line. Among the compounds, those with one amidino-substituent have shown the best effect. The most active benzo[b]thieno[2,3-c]quinolones induced apparent S and G2/M arrests of the cell cycle, which resulted in apoptosis. These results strongly suggest that the compounds may act as topoisimerase "poisons", which is in good agreement with their intercalative mode of binding to ds-DNA/RNA, in contrast to the studied "acyclic"group of derivatives. 6a and 6d showed the best selectivity by inhibiting the growth of tumor cells but not of normal fibroblasts.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D009570 Nitriles Organic compounds containing the -CN radical. The concept is distinguished from CYANIDES, which denotes inorganic salts of HYDROGEN CYANIDE. Nitrile
D004247 DNA A deoxyribonucleotide polymer that is the primary genetic material of all cells. Eukaryotic and prokaryotic organisms normally contain DNA in a double-stranded state, yet several important biological processes transiently involve single-stranded regions. DNA, which consists of a polysugar-phosphate backbone possessing projections of purines (adenine and guanine) and pyrimidines (thymine and cytosine), forms a double helix that is held together by hydrogen bonds between these purines and pyrimidines (adenine to thymine and guanine to cytosine). DNA, Double-Stranded,Deoxyribonucleic Acid,ds-DNA,DNA, Double Stranded,Double-Stranded DNA,ds DNA
D004354 Drug Screening Assays, Antitumor Methods of investigating the effectiveness of anticancer cytotoxic drugs and biologic inhibitors. These include in vitro cell-kill models and cytostatic dye exclusion tests as well as in vivo measurement of tumor growth parameters in laboratory animals. Anticancer Drug Sensitivity Tests,Antitumor Drug Screens,Cancer Drug Tests,Drug Screening Tests, Tumor-Specific,Dye Exclusion Assays, Antitumor,Anti-Cancer Drug Screens,Antitumor Drug Screening Assays,Tumor-Specific Drug Screening Tests,Anti Cancer Drug Screens,Anti-Cancer Drug Screen,Antitumor Drug Screen,Cancer Drug Test,Drug Screen, Anti-Cancer,Drug Screen, Antitumor,Drug Screening Tests, Tumor Specific,Drug Screens, Anti-Cancer,Drug Screens, Antitumor,Drug Test, Cancer,Drug Tests, Cancer,Screen, Anti-Cancer Drug,Screen, Antitumor Drug,Screens, Anti-Cancer Drug,Screens, Antitumor Drug,Test, Cancer Drug,Tests, Cancer Drug,Tumor Specific Drug Screening Tests
D005347 Fibroblasts Connective tissue cells which secrete an extracellular matrix rich in collagen and other macromolecules. Fibroblast
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000578 Amidines Derivatives of oxoacids RnE(
D000813 Anilides Any aromatic amide obtained by acylation of aniline.
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D012313 RNA A polynucleotide consisting essentially of chains with a repeating backbone of phosphate and ribose units to which nitrogenous bases are attached. RNA is unique among biological macromolecules in that it can encode genetic information, serve as an abundant structural component of cells, and also possesses catalytic activity. (Rieger et al., Glossary of Genetics: Classical and Molecular, 5th ed) RNA, Non-Polyadenylated,Ribonucleic Acid,Gene Products, RNA,Non-Polyadenylated RNA,Acid, Ribonucleic,Non Polyadenylated RNA,RNA Gene Products,RNA, Non Polyadenylated

Related Publications

Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
Novel derivatives of benzo[b]thieno[2,3-c]quinolones: synthesis, photochemical synthesis, and antitumor evaluation.
October 2003, Journal of medicinal chemistry,
Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno[3',2':4,5]thieno[2,3-c]quinolones.
May 2002, Chemical & pharmaceutical bulletin,
Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
Synthesis, photochemical synthesis, DNA binding and antitumor evaluation of novel cyano- and amidino-substituted derivatives of naphtho-furans, naphtho-thiophenes, thieno-benzofurans, benzo-dithiophenes and their acyclic precursors.
August 2006, European journal of medicinal chemistry,
Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
Facile and convenient synthesis of new thieno[2,3-b]-thiophene derivatives.
December 2010, Molecules (Basel, Switzerland),
Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
General synthesis of dinaphtho[2,3-b:2',3'-f]thieno[3,2-b]thiophene (DNTT) derivatives.
July 2011, Organic letters,
Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
Synthesis and chemical characterisation of new bis-thieno [2,3-b]thiophene derivatives.
May 2010, Molecules (Basel, Switzerland),
Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
Synthesis and antimicrobial activity of some new thieno[2,3-b]thiophene derivatives.
April 2013, Molecules (Basel, Switzerland),
Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
Synthesis of thiophene and N-substituted thieno[3,2-d] pyrimidine derivatives as potent antitumor and antibacterial agents.
September 2017, Acta pharmaceutica (Zagreb, Croatia),
Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
Chemical and photochemical synthesis of substituted dihydro-thieno[2',3':4,5]thieno[2,3-c]quinolin-6-ones and tetrahydro-dithieno[2,3-b:2',3'-d]thieno[2'',3''c:2'',3''c']diquinolin-6,14-dione.
January 2005, Molecules (Basel, Switzerland),
Ivana Jarak, and Marijeta Kralj, and Lidija Suman, and Gordana Pavlović, and Jasna Dogan, and Ivo Piantanida, and Mladen Zinić, and Kresimir Pavelić, and Grace Karminski-Zamola
Synthesis and pharmacological evaluation of thieno[2,3-b]pyridine derivatives as novel c-Src inhibitors.
April 2011, Bioorganic & medicinal chemistry,
Copied contents to your clipboard!