TY - JOUR
T1 - Synthesis and Antitumor Activity of 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-indoles and 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-7-azaindoles
AU - Diana, Patrizia
AU - Carbone, Anna
AU - Barraja, Paola
AU - Montalbano, Alessandra
AU - Parrino, Barbara
AU - Lopergolo, Alessia
AU - Pennati, Marzia
AU - Zaffaroni, Nadia
AU - Cirrincione, Girolamo
PY - 2011/7
Y1 - 2011/7
N2 - Given the potent antimicrobial, antiviral, and antitumor activities of many natural products, there is an increasing interest in the synthesis of new molecules based on natural compound scaffolds. Based on a 2,4-bis(3'-indolyl)imidazole skeleton, two new series of phenylthiazolylindoles and phenylthiazolyl-7-azaindoles were obtained by Hantzsch reaction between substituted phenylthioamides and the α-bromoacetyl derivatives. Some azaindole derivatives, tested at the National Cancer Institute against a panel of ∼60 tumor cell lines derived from nine human cancer cell types, showed inhibitory effects against all cell lines investigated at micromolar to nanomolar concentrations. Two of them exhibited a high affinity for CDK1, with IC50 values of 0.41 and 0.85μM. These promising results will set the foundation for future investigations into the development of anticancer therapies. Marine mining: Given the promise of marine-derived bioactive indole alkaloids, we synthesized a series of phenylthiazolylindoles and phenylthiazolyl-7-azaindoles, and evaluated their antitumor activity against a panel of 60 cancer cell lines. Some derivatives showed IC50 values in the micromolar to nanomolar range.
AB - Given the potent antimicrobial, antiviral, and antitumor activities of many natural products, there is an increasing interest in the synthesis of new molecules based on natural compound scaffolds. Based on a 2,4-bis(3'-indolyl)imidazole skeleton, two new series of phenylthiazolylindoles and phenylthiazolyl-7-azaindoles were obtained by Hantzsch reaction between substituted phenylthioamides and the α-bromoacetyl derivatives. Some azaindole derivatives, tested at the National Cancer Institute against a panel of ∼60 tumor cell lines derived from nine human cancer cell types, showed inhibitory effects against all cell lines investigated at micromolar to nanomolar concentrations. Two of them exhibited a high affinity for CDK1, with IC50 values of 0.41 and 0.85μM. These promising results will set the foundation for future investigations into the development of anticancer therapies. Marine mining: Given the promise of marine-derived bioactive indole alkaloids, we synthesized a series of phenylthiazolylindoles and phenylthiazolyl-7-azaindoles, and evaluated their antitumor activity against a panel of 60 cancer cell lines. Some derivatives showed IC50 values in the micromolar to nanomolar range.
KW - Antitumor agents
KW - Azaindoles
KW - Indoles
KW - Kinases
KW - Nortopsentins
UR - http://www.scopus.com/inward/record.url?scp=79959695729&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79959695729&partnerID=8YFLogxK
U2 - 10.1002/cmdc.201100078
DO - 10.1002/cmdc.201100078
M3 - Article
C2 - 21523912
AN - SCOPUS:79959695729
VL - 6
SP - 1300
EP - 1309
JO - ChemMedChem
JF - ChemMedChem
SN - 1860-7179
IS - 7
ER -