32358-83-1

Usage

InChI:InChI=1/C12H6O3/c13-10-7-3-1-2-4-8(7)12-9(11(10)14)5-6-15-12/h1-6H

Upstream product

• 148839-41-2 2-o-Tolyl-furan-3-carboxylic acid diethylamide 
• 82423-03-8 2-(1-hydroxy-1-methylethyl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 1198104-22-1 naphtho[1,2-b]furan-4-ol 
• 84-79-7 Lapachol 
• 107-20-0 2-chloroethanal 
• 106-99-0 buta-1,3-diene 
• 13196-10-6 benzofuran-5-ol 
• 858019-74-6 2-hydroxy-3-vinyl-[1,4]naphthoquinone 

Downstream Products

• 1192373-15-1 2-(4-formylphenyl)furo[3',2':3,4]naphtho[1,2-d]imidazole 
• 1192373-14-0 2-(4-nitrophenyl)furo[3',2':3,4]naphtho[1,2-d]imidazole 
• 1192373-13-9 2-phenylfuro[3',2':3,4]naphtho[1,2-d]imidazole 

Relevant academic research and scientific papers

Facile synthesis of avicequinone-B natural product

An efficient synthesis of avicequinone-B (2) and furonaphthoquinone 4 has been carried out starting from 2-hydroxy-1,4-naphthoquinone (6) by CAN-mediated cycloaddition reaction.

Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile

In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control β-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H … π interactions with Trp105 and Phe178 residues compared to the control β-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation.

Applications of naphtho[1,2-b]furan-4,5-diketone-2-sulfonic acid derivative and salt thereof in preparation of antitumor drugs

The invention discloses applications of a naphtho[1,2-b]furan-4,5-diketone-2-sulfonic acid derivative and a salt thereof in preparation of antitumor drugs, wherein the chemical structure formula of the naphtho[1,2-b]furan-4,5-diketone-2-sulfonic acid derivative is represented by a general formula (I), the general formula (I) is defined in the specification, R1 , R2, R3 and R4 are respectively and independently selected from hydrogen and halogen, and R5 is independently selected hydrogen, halogen, C1-C5 alkyl, and aryl. According to the present invention, the structure of the parent compound is modified, such that the water solubility of the compound is improved, and the good antitumor activity is provided.

Biomimetic in vitro oxidation of lapachol: A model to predict and analyse the in vivo phase i metabolism of bioactive compounds

The bioactive naphtoquinone lapachol was studied in vitro by a biomimetic model with Jacobsen catalyst (manganese(III) salen) and iodosylbenzene as oxidizing agent. Eleven oxidation derivatives were thus identified and two competitive oxidation pathways postulated. Similar to Mn(III) porphyrins, Jacobsen catalyst mainly induced the formation of para-naphtoquinone derivatives of lapachol, but also of two ortho-derivatives. The oxidation products were used to develop a GC-MS (SIM mode) method for the identification of potential phase I metabolites in vivo. Plasma analysis of Wistar rats orally administered with lapachol revealed two metabolites, α-lapachone and dehydro-α-lapachone. Hence, the biomimetic model with a manganese salen complex has evidenced its use as a valuable tool to predict and elucidate the in vivo phase I metabolism of lapachol and possibly also of other bioactive natural compounds.

Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra-cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids

Synthesis of phenanthro[1,2-b]furan-10,11-dione, the core nucleus present in Tanshinone-I is described in 8-10 steps starting from 2-bromo-3,4-dihydro-1- naphthaldehyde. The bromoaldehyde was converted to methyl 2-(2-bromo-1-naphthyl) acetate or 2-(2- bro

Furo[3′,2′:3,4]naphtho[1,2-d]imidazole derivatives as potential inhibitors of inflammatory factors in sepsis

Synthesis and anti-inflammatory effects of certain furo[3′,2′:3,4]naphtho[1,2-d]imidazole derivatives 12-18 were studied. These compounds were synthesized from naphtho[1,2-b]furan-4,5-dione (10) which in turn was prepared from the known 2-hydoxy-1,4-napht

Chemical constituents of Avicennia alba. Isolation and structural elucidation of new naphthoquinones and their analogues

Three new naphthoquinones and their analogues, named avicequinone-A (1), -B (2), -C (3), and avicenol-A (4), -B (5), -C (6), respectively, were isolated from the stem hark of Avicennia alba (Avicenniaceae) collected in Singapore, and their structures were elucidated by means of spectral methods. Gillan and co-workers have proposed that the structures of the new phytoalexins isolated from Avicennia marina are 1,2-naphthoquinones 8 and 9. Our synthetic and spectrometric studies showed that these structures should be revised respectively to 1,4-naphthoquinones 2 and 3, named avicequinone-B and -C by us.

COMBINED DIRECTED METALATION-CROSS COUPLING STRATEGIES. A REGIOSPECIFIC ROUTE TO HETERORING-ANNELATED ortho-NAPHTHOQUINONES AND A SHORT SYNTHESIS OF β-LAPACHONE

A general combined metalation-cross coupling methodology (Scheme 1) for the regiospecific construction of heteroring fused o-naphthoquinones 8 is described and its application to a short synthesis of the antimalarial/antitumor natural product β-lapachone (14) is demonstrated.