Heterocyclic Quinones from 2,3-Dichloro-1,4-naphthoquinone.

Sartori, Mario

doi:10.1021/cr60223a005

Cited by 48 publications

(13 citation statements)

References 26 publications

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“…Indolizino[1,2-b]quinoline derivatives, were prepared by Luckenbaugh et al 5 in a one-pot reaction by condensation of 2,3-dichloro-1,4-naphthoquinone and an active β-carbonilic compounds in presence of a high excess of pyridine and ethanol. However, the reaction yields showed high variability depending on β-carbonilic compounds, ranging from 15% for quinone 3 to 91% for quinone 1.…”

Section: Resultsmentioning

confidence: 99%

BIOLOGICAL ACTIVITIES AND CORRELATIONS TENDENCY OF ELECTROCHEMICAL PROPERTIES OF SOME INDOLIZINO[1,2-B]QUINOLINE DERIVATIVES

Cañete¹,

Armijo

Valle

et al. 2012

J. Chil. Chem. Soc.

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We report the preparation of a series of indolylquinone and pyridine derivatives in order to evaluate structure-activity relationships in human gastric (AGS), lung (SK-MES-1), bladder (J82) cancer cell lines and human normal lung fibroblasts (MCR-5). Two correlations tendency between half-wave redox potentials against their antineoplasic activity were found making it possible to establish that for epithelial human gastric cancer (AGS) cell lines and human normal lung fibroblasts (MCR-5). The quinone bioreduction should correspond to a one electron process under normomix conditions, whilst for all other lines this process should correspond to a two electron attachment via a hypoxic process.

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Section: Resultsmentioning

confidence: 99%

BIOLOGICAL ACTIVITIES AND CORRELATIONS TENDENCY OF ELECTROCHEMICAL PROPERTIES OF SOME INDOLIZINO[1,2-B]QUINOLINE DERIVATIVES

Cañete¹,

Armijo

Valle

et al. 2012

J. Chil. Chem. Soc.

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“…This avoids traditional multistage routes with 2,3-dihalo-1,4-naphthoquinones as starting materials (Sartori, 1962).…”

Section: Synthetic Methodsmentioning

confidence: 99%

Quinoid systems in chemistry and pharmacology

et al. 2015

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In this paper, we present a brief review of quinoid systems, focusing on their chemical synthesis over the last decade. We address not only major methods of synthesizing quinoids, but also their involvement in biological processes. We highlight their medical relevance and versatility, including antitumor, antiretroviral, or antihypertensive agents, properties determined by their various patterns of substitution. Graphical AbstractKeywords Quinone Á Synthesis Á Cytotoxicity Á Natural products Á Pharmacology Á Redox Abbreviations 3a-HSD 3a-Hydroxysteroid dehydrogenase AIDS Acquired Immune Deficiency Syndrome AlnA Alnumycin A AlnB Alnumycin B BAQ Benzanthracene quinone (7,12-benzo[a] anthraquinone) BPQ Benzo[a]pyrene-7,8-dione CAN Ceric ammonium nitrate CC 50 50 % Cytotoxic concentration CDC25 Cell division cycle phosphatases Cyt Ferricytochrome d-A 2 0 -Deoxyadenosine DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone d-G, d-Guo 2'-Deoxyguanosine DMF N,N-dimethylformamide DMP Dess-Martin periodinane DMSO

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“…2‐Hydroxy‐1,4‐naphthoquinone has been known for the past 4000 years, is found in many natural products and has been employed as a synthetic intermediate for the preparation of numerous heterocyclic compounds. Molecules containing the heterocyclic quinone group constitute one of the most important classes of compounds in organic chemistry because of their biological properties such as antitumor, antibacterial, antifungal and anti‐inflammatory activities …”

Section: Introductionmentioning

confidence: 99%

Zn( L‐proline)₂ as a powerful and reusable organometallic catalyst for the very fast synthesis of 2‐amino‐4H‐benzo[g]chromene derivatives under solvent‐free conditions

Maleki

Babaee

Tayebee

2015

Applied Organom Chemis

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Heterocyclic Quinones from 2,3-Dichloro-1,4-naphthoquinone.

Cited by 48 publications

References 26 publications

BIOLOGICAL ACTIVITIES AND CORRELATIONS TENDENCY OF ELECTROCHEMICAL PROPERTIES OF SOME INDOLIZINO[1,2-B]QUINOLINE DERIVATIVES

BIOLOGICAL ACTIVITIES AND CORRELATIONS TENDENCY OF ELECTROCHEMICAL PROPERTIES OF SOME INDOLIZINO[1,2-B]QUINOLINE DERIVATIVES

Quinoid systems in chemistry and pharmacology

Zn( L‐proline)₂ as a powerful and reusable organometallic catalyst for the very fast synthesis of 2‐amino‐4H‐benzo[g]chromene derivatives under solvent‐free conditions

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Heterocyclic Quinones from 2,3-Dichloro-1,4-naphthoquinone.

Cited by 48 publications

References 26 publications

BIOLOGICAL ACTIVITIES AND CORRELATIONS TENDENCY OF ELECTROCHEMICAL PROPERTIES OF SOME INDOLIZINO&#091;1,2-B]QUINOLINE DERIVATIVES

BIOLOGICAL ACTIVITIES AND CORRELATIONS TENDENCY OF ELECTROCHEMICAL PROPERTIES OF SOME INDOLIZINO&#091;1,2-B]QUINOLINE DERIVATIVES

Quinoid systems in chemistry and pharmacology

Zn( L‐proline)2 as a powerful and reusable organometallic catalyst for the very fast synthesis of 2‐amino‐4H‐benzo[g]chromene derivatives under solvent‐free conditions

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BIOLOGICAL ACTIVITIES AND CORRELATIONS TENDENCY OF ELECTROCHEMICAL PROPERTIES OF SOME INDOLIZINO[1,2-B]QUINOLINE DERIVATIVES

BIOLOGICAL ACTIVITIES AND CORRELATIONS TENDENCY OF ELECTROCHEMICAL PROPERTIES OF SOME INDOLIZINO[1,2-B]QUINOLINE DERIVATIVES

Zn( L‐proline)₂ as a powerful and reusable organometallic catalyst for the very fast synthesis of 2‐amino‐4H‐benzo[g]chromene derivatives under solvent‐free conditions