106835-44-3Relevant articles and documents
IND-2, a pyrimido[1″,2″:1,5]pyrazolo[3,4-b]quinoline derivative, circumvents multi-drug resistance and causes apoptosis in colon cancer cells
Karthikeyan, Chandrabose,Lee, Crystal,Moore, Joshua,Mittal, Roopali,Suswam, Esther A.,Abbott, Kodye L.,Pondugula, Satyanarayana R.,Manne, Upender,Narayanan, Narayanan K.,Trivedi, Piyush,Tiwari, Amit K.
, p. 602 - 611 (2015)
Naturally occurring condensed quinolines have anticancer properties. In efforts to find active analogues, we designed and synthesized eight polycyclic heterocycles with a pyrimido[1″,2″:1,5]pyrazolo[3,4-b]quinoline framework (IND series). The compounds were evaluated for activity against colon (HCT-116 and S1-MI-80), prostate (PC3 and DU-145), breast (MCF-7 and MDAMB-231), ovarian (ov2008 and A2780), and hepatocellular (HepG2) cancer cells and against non-cancerous Madin Darby canine kidney (MDCK), mouse embryonic fibroblast (NIH/3T3), and human embryonic kidney cells (HEK293). IND-2, a 4-chloro-2-methyl pyrimido[1″,2″:1,5]pyrazolo[3,4-b]quinoline, exhibited more than ten-fold selectivity and potent cytotoxic activity against colon cancer cells relative to the other cancer and non-cancer cells. With five additional colon cancer cell lines (HT-29, HCT-15, LS-180, LS-174, and LoVo), IND-2 had similar cytotoxicity and selectivity, and sub-micromolar concentrations caused changes in the morphology of HCT-116 and HCT-15 cells. IND-2 did not activate the transactivating function of the pregnane X receptor (PXR), indicating that it does not induce PXR-regulated ABCB1 or ABCG2 transporters. Indeed, IND-2 was not a substrate of ABCB1 or ABCG2, and it induced cytotoxicity in HEK293 cells overexpressing ABCB1 or ABCG2 to the same extent as in normal HEK293 cells. IND-2 was cytotoxic to resistant colon carcinoma S1-MI-80 cells, approximately three- and five-fold more than SN-38 and topotecan, respectively. In HCT-116 colon cancer cells, IND-2 produced concentration-dependent changes in mitochondrial membrane potential, leading to apoptosis, and sub-micromolar concentrations caused chromosomal DNA fragmentation. These findings suggest that, by increasing apoptosis, IND-2 has potential therapeutic efficacy for colorectal cancer.
Ru(III)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources
Cui, Xiuling,Han, Xiliang,Hu, Di,Hu, Wei,Pi, Chao,Wu, Yangjie
, (2022/01/28)
A Ru(Ⅲ)-catalyzed annulation reaction of 2-aminoaromatic aldehydes (ketones) and isoxazoles to afford diverse 3-cyanoquinolines has been developed. Notably, isoxazole acted as a cyclization reagent and nontoxic cyano source via N-O bond cleavage and fragm
Design, synthesis, and docking study of new quinoline derivatives as antitumor agents
Nasr, Eman E.,Mostafa, Amany S.,El-Sayed, Magda A. A.,Massoud, Mohammed A. M.
, (2019/05/21)
New quinolines substituted with various heterocycles and chalcone moieties were synthesized and evaluated as antitumor agents. All the synthesized compounds were in vitro screened against 60 human cancer cell lines. Compound 13 showed the highest cytotoxi
lH-Pyrazolo[3,4-b]quinolin-3-amine derivatives inhibit growth of colon cancer cells via apoptosis and sub G1 cell cycle arrest
Karthikeyan, Chandrabose,Amawi, Haneen,Viana, Arabela Guedes,Sanglard, Leticia,Hussein, Noor,Saddler, Maria,Ashby, Charles R.,Moorthy, N.S. Hari Narayana,Trivedi, Piyush,Tiwari, Amit K.
, p. 2244 - 2249 (2018/05/31)
A series of lH-pyrazolo[3,4-b]quinolin-3-amine derivatives were synthesized and evaluated for anticancer efficacy in a panel of ten cancer cell lines, including breast (MDAMB-231 and MCF-7), colon (HCT-116, HCT-15, HT-29 and LOVO), prostate (DU-145 and PC3), brain (LN-229), ovarian (A2780), and human embryonic kidney (HEK293) cells, a non-cancerous cell line. Among the eight derivatives screened, compound QTZ05 had the most potent and selective antitumor efficacy in the four colon cancer cell lines, with IC50 values ranging from 2.3 to 10.2 μM. Furthermore, QTZ05 inhibited colony formation in HCT-116 cells in a concentration-dependent manner. Cell cycle analysis data indicated that QTZ05 caused an arrest in the sub G1 cell cycle in HCT-116 cells. QTZ05 induced apoptosis in HCT-116 cells in a concentration-dependent manner that was characterized by chromatin condensation and increase in the fluorescence of fluorochrome-conjugated Annexin V. The findings from our study suggest that QTZ05 may be a valuable prototype for the development of chemotherapeutics targeting apoptotic pathways in colorectal cancer cells.
Synthesis of novel pyrazoloquinolines
Praveen Kumar Darsi,Shiva Kumar,Rama Devi,Naidu,Dubey
, p. 237 - 244 (2013/09/24)
The synthesis of novel pyrazoloquinolines, 3-(1H-pyrazolo [3,4-6] quinolin-3-ylimino) indolin-2-one (5) and 1-methyl-3-(1-methyl-1H-pyrazolo [3,4-b] quinolin-3-ylimino)-1,3-dihydro-indol-2-one (6) is described. Reaction of 2-chloroquinolin-3-carboxaldehyd
Pyrazolo-fused quinoline analogues: Synthesis of 1H-pyrazolo [3, 4-b] quinolines and 3-amino-1H-pyrazolo [3, 4-b] quinolines from 3-formyl and 3-cyano-2-chloroquinolines
Srivastava, Ambika,Singh, Mrityunjay K.,Singh
, p. 292 - 296 (2007/10/03)
Stepwise synthesis of 1H-pyrazolo [3, 4-b] quinolines 6 has been described from the reactions of 2-chloro-3-formylquinolines 1 with ethyleneglycol and hydrazine hydrate reagents in sequence followed by hydrolysis with BiCl 3. However, 3-amino-1H-pyrazolo[3, 4-b]quinolines 7 have been synthesized from 2-chloro-3-cyanoquinolines 2 with excess of hydrazine hydrate in one step. The functional group manipulation of amino group in compounds 7 has also been studied.
Evaluation of some pyrazoloquinolines as inhibitors of herpes simplex virus type 1 replication
Bekhit, Adnan A.,El-Sayed, Ola A.,Aboul-Enein, Hassan Y.,Siddiqui, Yunus M.,Al-Ahdal, Mohammed N.
, p. 74 - 77 (2007/10/03)
Three structurally related aminopyrazoloquinoline derivatives were evaluated for their antiviral activity against Herpes Simplex virus type 1. These compounds were examined for their in vitro antiviral activity by two different bioassays, namely; crystal violet staining and tetrazolium dye (MTS) measurement. The antiviral role of these compounds was confirmed by enumerating the infectious particles with plaque assay. The acute toxicity values of the biologically active compounds were determined prior to their screening as antiviral agents.
Synthesis and antimicrobial activity of novel pyrazolo[3,4-b]quinoline derivatives
El-Sayed, Ola A.,Aboul-Enein, Hassan Y.
, p. 117 - 120 (2007/10/03)
New pyrazolo[3,4-b]quinoline derivatives have been prepared by cyclization of the intermediate 2-chloroquinoline-3-carbonitrile 7, namely 3-amino-1H-pyrazolo[3,4-b]quinoline 8a, 3-amino-1phenyl/(p-substituted)phenyl/-1H-pyrazolo[3,4-b]-quinoline 8bf. Furthermore, 3-[(3-aryl-4-oxothiazolidin-2-ylidene)amino]1H-pyrazolo[3,4-b]quinolines 11a,b; 3-[(3-aryl-4-oxothiazin-2ylidene)amino]-1H-pyrazolo[3,4-b]quinolines 12a,b and 3-(2aryl-4-oxothiazolidin-3-yl)- 1H-pyrazolo[3,4-b]quinolines 13a,b were synthesized. The antimicrobial activity was evaluated for most of the prepared compounds.
Synthesis of new pyrazolo[3,4-b]quinolines, thieno[2,3-b]quinolines and related condensed heterocyclic systems
Bakhite, Etify Abdel-Ghafar
, p. 1175 - 1183 (2007/10/03)
3-Amino-l H-pyrazolo[3,4-b]quinoline (2) was reacted with benzaldehyde, acetylacetone, ethyl aceto-acetate and/or phenyl isothiocyanate to give compounds 3,4,5 and 6, respectively. The interaction of 6 with some α-haloesters and/or α-haloketones produced the corresponding thiazolidinones 7a-c and thiazolines 9a-d. lH-Pyrazolo[3,4-b]quinoline-3-diazonium chloride (11) was coupled with some active methylene compounds to give the corresponding hydrazono compounds 12a, b and 13 which, in turn were cyclized into the corresponding triazinopyrazoloquinolines 14a,b and 15 by heating in acetic acid. 3-Aminothieno[2,3-b]quinoline-2-carbohydrazide (19) and 3-amino-2-(1H-benzimidazol-2-yl)thieno[2,3-b]quinoline (21) were prepared and employed as key intermediates for synthesizing the second class of the title compounds.
Syntheses of Substituted Pyrazoloquinolines, 3,4-Dihydro-4-oxopyrimidothienoquinoline and Pyridopyrimidoquinoline
Neelima,Bhat, Balkrisen,Bhaduri, Amiya Prasad
, p. 925 - 928 (2007/10/02)
Syntheses of substituted pyrazoloquinolines, 3,4-dihydro-4-oxopyrimidothienoquinoline and 12-phenylpyridopyrimidoquinoline are described.
