naphtho(2,3-b)furan-4,9-dione

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Description

naphtho(2,3-b)furan-4,9-dione: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	79740
CHEMBL ID	62539
SCHEMBL ID	28782
MeSH ID	M0199590

Synonyms (11)

Synonym
naphtho(2,3-b)furan-4,9-dione
npf-4,9-dione
avicequinone-b
CHEMBL62539
5656-82-6
naphtho[2,3-b]furan-4,9-dione
benzo[f][1]benzofuran-4,9-dione
SCHEMBL28782
4h,9h-naphtho[2,3-b]furan-4,9-dione
furan, 2,3-(1,2-phenylenedicarbonyl)-
DTXSID00205114

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (36)

Assay ID	Title	Year	Journal	Article
AID702314	Activity of human recombinant NQO-1 assessed as rate of superoxide generation measuring SOD-inhibitable reduction of succinoylated cytochrome c per unit enzyme at 25 umol/ml by spectrophotometry in presence of catalase and DTPA (Rvb = 0.2 +/- 0.1 micomol/	2012	Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16	Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular genera
AID1356022	Antiproliferative activity against human K562 cells measured after 48 hrs by MTT assay	2018	Journal of natural products, 07-27, Volume: 81, Issue:7	Napabucasin and Related Heterocycle-Fused Naphthoquinones as STAT3 Inhibitors with Antiproliferative Activity against Cancer Cells.
AID336958	Cytotoxicity against human Raji cells assessed as cell viability at 500 molar ratio
AID336954	Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 500 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID492235	Cell cycle arrest in human K562 cells assessed as accumulation at G0/G1 phase at 1 uM after 24 hrs using propidium iodide staining by flow cytometry	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID492228	Cytotoxicity against human SF268 cells after 72 hrs by XTT assay	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID492237	Cell cycle arrest in human K562 cells assessed as accumulation at G2/M phase at 1 uM after 24 hrs using propidium iodide staining by flow cytometry	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID336955	Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 100 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID336959	Cytotoxicity against human Raji cells assessed as cell viability at 100 molar ratio
AID492229	Cytotoxicity against human Detroit 551 cells after 72 hrs by XTT assay	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID702315	Induction of superoxide generation in human HaCaT cells at 50 uM after 30 min by flow cytometry (Rvb = 7.1 +/- 5.2 )	2012	Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16	Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular genera
AID702316	Activity of human recombinant cytochrome P450 reductase assessed as rate of superoxide generation measuring SOD-inhibitable reduction of succinoylated cytochrome c per 2 mU enzyme at 100 umol/ml by spectrophotometry in presence of catalase and DTPA (Rvb =	2012	Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16	Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular genera
AID492234	Selectivity index, ratio of GI50 for human Detroit 551 cells to GI50 for human K562 cells	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID492238	Cell cycle arrest in human K562 cells assessed as accumulation at Sub-G1 phase at 1 uM after 24 hrs using propidium iodide staining by flow cytometry	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID492231	Selectivity index, ratio of GI50 for human Detroit 551 cells to GI50 for human NCI-H460 cells	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID702313	Induction of superoxide generation in human HaCaT cells at 5 micomol/L after 18 hrs by flow cytometry (Rvb = 367.5 +/- 80.1 )	2012	Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16	Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular genera
AID380221	Growth inhibition of Yeast expressing rad52.top1 mutant by yeast bioassay	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Synthesis of furanonaphthoquinones with hydroxyamino side chains.
AID492236	Cell cycle arrest in human K562 cells assessed as accumulation at S phase at 1 uM after 24 hrs using propidium iodide staining by flow cytometry	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID492227	Cytotoxicity against human NCI-H460 cells after 72 hrs by XTT assay	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID492225	Cytotoxicity against human SF268 cells at 4 ug/ml after 48 hrs by sulforhodamine B assay relative to control	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID492223	Cytotoxicity against human MCF7 cells at 4 ug/ml after 48 hrs by sulforhodamine B assay relative to control	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID1356021	Antiproliferative activity against human MDA-MB-231 cells measured after 48 hrs by MTT assay	2018	Journal of natural products, 07-27, Volume: 81, Issue:7	Napabucasin and Related Heterocycle-Fused Naphthoquinones as STAT3 Inhibitors with Antiproliferative Activity against Cancer Cells.
AID380222	Growth inhibition of Yeast expressing rad52 mutant by yeast bioassay	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Synthesis of furanonaphthoquinones with hydroxyamino side chains.
AID336960	Cytotoxicity against human Raji cells assessed as cell viability at 10 molar ratio
AID336957	Cytotoxicity against human Raji cells assessed as cell viability at 1000 molar ratio
AID492232	Selectivity index, ratio of GI50 for human Detroit 551 cells to GI50 for human SF268 cells	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID492226	Cytotoxicity against human MCF7 cells after 72 hrs by XTT assay	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID380223	Cytotoxicity against rat H4IIE cells by XTT assay	1999	Journal of natural products, Jul, Volume: 62, Issue:7	Synthesis of furanonaphthoquinones with hydroxyamino side chains.
AID492233	Cytotoxicity against human K562 cells after 72 hrs by XTT assay	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID336953	Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 1000 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID702317	Cytotoxicity against human HaCaT cells assessed as LDH release at 2 uM after 4 hrs by UV method	2012	Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16	Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular genera
AID336956	Inhibition of TPA-induced EBV-early antigen activation in human Raji cells at 10 molar ratio after 48 hrs by indirect immunofluorescence technique relative to TPA
AID492230	Selectivity index, ratio of GI50 for human Detroit 551 cells to GI50 for human MCF7 cells	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID492224	Cytotoxicity against human NCI-H460 cells at 4 ug/ml after 48 hrs by sulforhodamine B assay relative to control	2010	Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14	Synthesis and antiproliferative evaluation of certain iminonaphtho[2,3-b]furan derivatives.
AID702318	Antihyperproliferative activity against human HaCaT cells after 48 hrs by phase contrast microscopy	2012	Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16	Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular genera
AID702312	Activity in dicoumarol-treated human HaCaT cells assessed as superoxide generation by flow cytometry (Rvb = 407.59 +/- 68.7 )	2012	Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16	Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular genera
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	2 (22.22)	18.2507
2000's	2 (22.22)	29.6817
2010's	5 (55.56)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.27

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	12.27 (24.57)
Research Supply Index	2.40 (2.92)
Research Growth Index	4.66 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.27)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	10 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
anthralin Anthralin: An anthracene derivative that disrupts MITOCHONDRIA function and structure and is used for the treatment of DERMATOSES, especially PSORIASIS. It may cause FOLLICULITIS.. anthralin : An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.	2.07	1	anthracenes	antipsoriatic
lapachol lapachol : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae.	2.17	1
beta-lapachone beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase. beta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.	2.52	2	benzochromenone; orthoquinones	anti-inflammatory agent; antineoplastic agent; plant metabolite
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	2.07	1	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.05	1	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	2.05	1	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
alpha-lapachone alpha-lapachone: structure in first source	2.17	1	organic heterotricyclic compound; organooxygen compound
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	3.13	5
2-methylnaphtho(2,3-b)furan-4,9-dione [no description available]	2.07	1
2-acetylfuranonaphthoquinone 2-acetylfuranonaphthoquinone: has antineoplastic activity; structure in first source	2.52	2

Condition	Relationship Strength	Studies
Experimental Hepatoma [description not available]	2	1
Benign Neoplasms [description not available]	2.05	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.05	1
Palmoplantaris Pustulosis [description not available]	2.07	1
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	2.07	1

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