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11H‑Pyrido[3′,2′:4,5]pyrrolo[3,2‑c]cinnoline and Pyrido[3′,2′:4,5]pyrrolo[1,2‑c][1,2,3]benzotriazine: Two New Ring Systems with Antitumor Activity

2014

Derivatives of new ring systems 11H-pyrido[3',2':4,5]pyrrolo[3,2-c]cinnoline and pyrido[3',2':4,5]pyrrolo[1,2-c][1,2,3]benzotriazine have been prepared from the key intermediates 2-(1H-pyrrolo[2,3-b]pyridin-2-yl)anilines in excellent yields (94-99%) and screened by the National Cancer Institute (Bethesda, MD) on about 60 human tumor cell lines derived from nine cancer cell types. The tested compounds exhibited antiproliferative activity against all the human cell lines, showing comparable MG_MID (mean graph midpoint) values in the range of 0.74-1.15 μM. A particular efficacy was observed against the leukemia subpanel (GI50 = 0.73-0.0090 μM). Flow cytometric analysis of the cell cycle demons…

StereochemistryCinnolines; triazinesChemistry PharmaceuticalAntineoplastic AgentsApoptosisHeterocyclic Compounds 2-RingHeterocyclic Compounds 4 or More Ringschemistry.chemical_compoundJurkat CellsCell Line TumorNeoplasmsDrug DiscoverytriazinesHumansCinnolineCell Proliferationchemistry.chemical_classificationReactive oxygen speciesCell DeathChemistryCell growthCell CycleCell MembraneTemperatureDepolarizationCell cycleCaspase InhibitorsMitochondriaEnzyme ActivationCell cultureApoptosisCaspasesCinnolines triazinesCancer cellMolecular MedicineLysosomesReactive Oxygen SpeciesCinnolines
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Synthesis and cytotoxic activity of novel C7-functionalized spongiane diterpenes.

2003

Based on two lead cytotoxic spongiane diterpenes, a new series of C7-oxygenated derivatives were synthesized and evaluated for their antitumor activity in vitro against the cancer cell lines HeLa and HEp-2. In general, introduction of either hydroxyl or acetoxy groups at C-7 did not improve the resultant cytotoxicity, while the presence of a butyrate ester led to more active compounds (CC(50)=4.0-9.5 microM).

StereochemistryClinical BiochemistryPharmaceutical ScienceAntineoplastic AgentsButyrateBiochemistryChemical synthesisHeLachemistry.chemical_compoundInhibitory Concentration 50Structure-Activity RelationshipCell Line TumorDrug DiscoveryStructure–activity relationshipHumansCytotoxicityMolecular Biologychemistry.chemical_classificationbiologyMolecular StructureOrganic Chemistrybiology.organism_classificationButyrateschemistryMolecular MedicineHemiacetalDiterpeneDiterpenesDrug Screening Assays AntitumorLactoneHeLa CellsBioorganicmedicinal chemistry
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Regioselective substitution of 6,7-dichloroquinoline-5,8-dione: synthesis and X-ray crystal structure of 4a,10,11-triazabenzo[3,2-a]fluorene-5,6-dion…

2003

6,7-Dichloroquinoline-5,8-dione (1) was reacted with a number of 2-aminopyridine derivatives. Of the several possible products of this reaction, 4a,10,11-triazabenzo[3,2-a]fluorene-5,6-dione (6), produced by condensation and rearrangement, was obtained as the major product, and its structure was subsequently unambigously determined by X-ray crystallographic study. Ortho-quinones were produced via nucleophilic substitution at position C7, which was unexpected, considering that para-quinones were produced via C6 substitution in the reaction between compound 1 and ethyl acetoacetate in our previous work. Such unexpected nucleophilic substitution at C7 provides an effective, yet simple route, t…

StereochemistryClinical BiochemistryPharmaceutical ScienceAntineoplastic AgentsCrystallography X-RayBiochemistryMedicinal chemistryChemical synthesisInhibitory Concentration 50chemistry.chemical_compoundNucleophilic aromatic substitutionDrug DiscoveryTumor Cells CulturedNucleophilic substitutionHumansMolecular BiologySubstitution reactionFluorenesMolecular StructureOrganic ChemistryQuinonesRegioselectivityStereoisomerismQuinonechemistryDoxorubicinEthyl acetoacetateQuinolinesMolecular MedicineAcid hydrolysisDrug Screening Assays AntitumorBioorganic & Medicinal Chemistry
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Activity of lupane triterpenoids from Maytenus species as inhibitors of nitric oxide and prostaglandin E2

2005

In the present study, we report that three new lupane triterpenes (1-3), in addition to 16 known ones (4-19), were isolated from the root bark of Maytenus cuzcoina and the leaves of Maytenus chiapensis. Their structures were elucidated by spectral analysis, including homonuclear and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC, and HMBC). The natural compounds and derivatives 6a, 6b, 9a, and 9b have been tested for potential anti-inflammatory activity, and several compounds including 3-epicalenduladiol (2), 11alpha-hydroxy-glochidone (3), rigidenol (6), acetoxy-rigidenol (6a), 11alpha-acetoxy-30-chloro-3-oxo-lup-20(29)-ene (6b), betulin (9), 28-acetoxy-betulin (9a), epibetul…

StereochemistryClinical BiochemistryPharmaceutical SciencePharmacognosyNitric OxideBiochemistryDinoprostoneTerpeneCelastraceaeMiceStructure-Activity Relationshipchemistry.chemical_compoundTriterpeneDrug DiscoveryAnimalsMolecular Biologychemistry.chemical_classificationBetulinbiologyMaytenusMacrophagesSpectrum AnalysisOrganic ChemistryBiological activityBacterial InfectionsMaytenusbiology.organism_classificationAntineoplastic Agents PhytogenicTriterpenesTerpenoidEndotoxinsPlant LeaveschemistryMolecular MedicineBioorganic & Medicinal Chemistry
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Synthesis and cytotoxicity of 6,11-Dihydro-pyrido- and 6,11-Dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives

2003

6,11-Dihydro-pyrido[2,3-b]phenazine-6,11-diones and 6,11-dihydro-benzo[2,3-b]phenazine-6,11-diones were synthesized from 6,7-dichloro-5,8-quinolinedione and 2,3-dichloro-1,4-naphthoquinone. The study on the cytotoxicity on these products revealed that the pyridophenazinediones, tetracyclic heteroquinone analogues with three nitrogen atoms exhibited a high cytotoxicity on several human tumor cell lines. Compound 9c and 9e showed in vitro antitumor activity comparable or superior to doxorubicin against the human ovarian tumor cells (SK-OV-3) and the human CNS cells (XF 498). The IC(50) value for compound 9e was 0.06 microM against the human CNS cells (XF 498), which was 2.6 times higher than …

StereochemistryClinical BiochemistryPhenazinePharmaceutical ScienceAntineoplastic AgentsCrystallography X-RayBiochemistryChemical synthesisInhibitory Concentration 50Structure-Activity Relationshipchemistry.chemical_compoundDrug DiscoveryTumor Cells CulturedNucleophilic substitutionHumansStructure–activity relationshipCytotoxicityMolecular BiologyMolecular StructureOrganic ChemistryIn vitroQuinonechemistryDoxorubicinCell cultureQuinolinesPhenazinesMolecular MedicineDrug Screening Assays AntitumorNaphthoquinonesBioorganic & Medicinal Chemistry
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Gamma-lactone-Functionalized antitumoral acetogenins are the most potent inhibitors of mitochondrial complex I.

2001

To study the relevance of the terminal alpha,beta-unsaturated gamma-methyl-gamma-lactone moiety of the antitumoral acetogenins of Annonaceae for potent mitochondrial complex I inhibition, we have prepared a series of semisynthetic acetogenins with modifications only in this part of the molecule, from the natural rolliniastatin-1 (1) and cherimolin-1 (2). Some of the hydroxylated derivatives (1b, 1d and 1e) in addition to two infrequent natural beta-hydroxy gamma-methyl gamma-lactone acetogenins, laherradurin (3) and itrabin (4), are more potent complex I inhibitors than any other known compounds.

StereochemistryClinical BiochemistrySubmitochondrial ParticlesPharmaceutical ScienceAntineoplastic AgentsMitochondrionBiochemistryMitochondria HeartLactonesMagnoliopsidaMultienzyme ComplexesDrug DiscoveryMoietyAnimalsNADH NADPH OxidoreductasesFuransMolecular Biologychemistry.chemical_classificationElectron Transport Complex IbiologyMolecular StructureOrganic ChemistryBiological activitybiology.organism_classificationIn vitroEnzymechemistryEnzyme inhibitorAnnonaceaebiology.proteinMolecular MedicineCattleLactoneBioorganicmedicinal chemistry letters
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Synthesis and in vitro antileukemic activity of new 4-triazenopyrazole derivatives

2003

Several new 4-(3,3-dimethyltriazeno)-5-benzamidopyrazole derivatives were prepared by reacting 4-diazo-5-benzamidopyrazole derivatives with dimethylamine. The compounds were tested at 10 microM for their vitro antileukemic activity against K562 (Human chronic myelogenous leukemia) and Raji (human Burkitt limphoma ) cell lines. Dacarbazine and methotrexate were used for comparative purpose. The 3-methyl-4-(3,3-dimethyltriazeno)-5-(substituted benzamido)pyrazoles, bearing the pyrazole nucleus free at 1 position, resulted more active than the 1-(substituted phenyl)-3-methyl-4-(3,3-dimethyltriazeno)-5-benzamidopyrazoles. Dacarbazine at 10 microM showed no activity in the above tests. The observ…

StereochemistryDacarbazinePharmaceutical ScienceAntineoplastic AgentsPyrazoleSettore BIO/19 - Microbiologia GeneraleInhibitory Concentration 50Structure-Activity Relationshipchemistry.chemical_compoundCytochrome P-450 Enzyme SystemCell Line TumorLeukemia Myelogenous Chronic BCR-ABL PositiveDrug DiscoverymedicineHumansDimethylamine4-Triazenopyrazoles Antiproliferative activity In vitro antileukemic acitivityDemethylationTriazinesGeneral MedicineBurkitt LymphomaSettore CHIM/08 - Chimica FarmaceuticaIn vitroRaji cellchemistryMechanism of actionPyrazolesGrowth inhibitionmedicine.symptommedicine.drugIl Farmaco
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Cytotoxic activity of diterpenoids isolated from the aerial parts of Elaeoselinum asclepium subsp. meoides.

2008

The phytochemical investigation of the acetone extract of the aerial parts of Elaeoselinum asclepium (L.) Bertol. subsp. meoides (Desf.) Fiori afforded several known diterpenoids as well as meoidic acid ( 5), new in the literature. The cytotoxic activities of elasclepic acid ( 1), ENT-atis-16-en-19-oic acid ( 2), ent-beyer-15-en-19-oic acid ( 3), ent-kaur-16-en-19-oic acid ( 4) and meoidic acid ( 5) were investigated on rat glioma C6 cells by evaluation of cell growth inhibition.

StereochemistryElaeoselinum asclepium subsp. meoides Umbelliferae diterpenoids meoidic acid cytotoxic activityPharmaceutical ScienceBiologyPharmacognosyAnalytical Chemistrychemistry.chemical_compoundCell Line TumorDrug Discoveryotorhinolaryngologic diseasesAcetoneCytotoxic T cellAnimalsCytotoxicityCell ProliferationPharmacologyMolecular StructureOrganic ChemistrySettore CHIM/06 - Chimica OrganicaElaeoselinum asclepium subsp. meoidesAntineoplastic Agents PhytogenicTerpenoidRatsComplementary and alternative medicinechemistryPhytochemicalMolecular MedicineDiterpeneDiterpenesApiaceaePlanta medica
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Pyrrolo[2,3-h]quinolinones: synthesis and photochemotherapic activity.

2003

A series of derivatives of the new ring system pyrrolo[2,3-h]quinoline-2-one was synthesized and evaluated as photoreagents toward cultured human tumor cells. Remarkable phototoxycity resulted for some derivatives, especially those bearing the phenyl group at the 7-position.

StereochemistryFibrosarcomaClinical BiochemistryPharmaceutical ScienceAntineoplastic AgentsQuinolonesRing (chemistry)BiochemistryChemical synthesischemistry.chemical_compoundStructure-Activity RelationshipDrug DiscoveryTumor Cells CulturedPhenyl groupHumansPhotosensitizerPyrrolesMolecular BiologyPhotosensitizing AgentsChemistryOrganic ChemistryGeneral MedicineIn vitroHuman tumorPhotochemotherapyCell cultureLactamMolecular MedicineDrug Screening Assays AntitumorBioorganicmedicinal chemistry letters
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Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistan…

2014

Abstract Malaria and cancer cause the death of millions of people every year. To combat these two diseases, it is important that new pharmaceutically active compounds have the ability to overcome multidrug resistance in cancer and Plasmodium falciparum strains. In search of effective anti-cancer and anti-malaria hybrids that possess improved properties compared to their parent compounds, a series of novel 1,2,4-trioxane-based hybrids incorporating egonol and/or ferrocene fragments were synthesized and tested in vitro against P. falciparum strains, CCRF–CEM cells and the multidrug-resistant P-glycoprotein-over-expressing CEM/ADR5000 cells. The most active compounds against P. falciparum stra…

StereochemistryMetallocenesPlasmodium falciparumAntineoplastic Agentschemistry.chemical_compoundAntimalarialsHeterocyclic CompoundsDrug DiscoverymedicineCytotoxic T cellHumansCell LineageFerrous CompoundsArtemisininMalaria FalciparumCytotoxicityIC50BenzofuransPharmacologyLeukemiabiologyOrganic ChemistryPlasmodium falciparumGeneral Medicinemedicine.diseasebiology.organism_classificationDrug Resistance MultipleMultiple drug resistanceLeukemiachemistryBiochemistry124-TrioxaneDrug Resistance Neoplasmmedicine.drugEuropean journal of medicinal chemistry
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