55481-88-4

Usage

Uses

Mollugin is an anti-tumor agent inducing apoptosis and autophagy in various cancer models.

InChI:InChI=1/C17H16O4/c1-17(2)9-8-12-13(16(19)20-3)14(18)10-6-4-5-7-11(10)15(12)21-17/h4-9,18H,1-3H3

Upstream product

• 60657-93-4 methyl 6-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo-[h]chromene-5-carboxylate 
• 873531-15-8 1,4-dimethoxy-3-(3-methyl-but-2-enyl)-naphthalene-2-carboxylic acid methyl ester 
• 97400-66-3 methyl 6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5-carboxylate 
• 83575-14-8 2-methoxycarbonyl-1,4-naphthoquinone 
• 104108-29-4 prenyl tributylstannane 
• 78570-30-6 3-(3-methyl-but-2-enyl)-1,4-dioxo-1,4-dihydro-naphthalene-2-carboxylic acid methyl ester 
• 1010732-35-0 methyl 6-(methoxymethoxy)-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate 
• 763-32-6 2-methyl-1-buten-4-ol 
• 31519-22-9 1,4-dihydroxy-2-naphthoic acid 
• 77060-74-3 methyl 1,4-dihydroxy-2-naphthoate 
• 115-18-4 2-methyl-3-buten-2-ol 
• 909576-31-4 2-(2,3-epoxy-3-methylbutyl)-1,4-naphthoquinone 
• 645413-83-8 6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol 
• 909576-35-8 5-bromo-6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran 

Downstream Products

• 1025006-46-5 methyl 6-benzyloxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate 

Relevant academic research and scientific papers

Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities

Novel and diverse mollugin analogues (1-12) were synthesized using PhB(OH)2/AcOH-mediated electrocyclization reaction as a key step. The newly synthesized compounds were screened for antioxidant and antibacterial activities. Compounds 1, 2, 5, 6, 8, and 10-12 showed high antioxidant activities in DPPH inhibition (IC50 = 0.52-1.11 μM) compared with BHT (IC50 = 9.67 μM). Compounds 3 exhibited potent antibacterial activity against Staphylococcus aureus (KCTC-1916) bacterial strain at 100 μg/mL. Structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR data and high-resolution mass spectrometry.

Pericyclic reactions of prenylated naphthoquinones: Biomimetic syntheses of mollugin and microphyllaquinone

(Chemical Equation Presented) A total synthesis of the bioactive naphthohydroquinone mollugin and the related naphthoquinone dimer microphyllaquinone is described. Both syntheses exploit the propensity of prenylated quinones to undergo tautomerization/oxa 6π-electrocyclizations.

CF3-substituted mollugin 2-(4-morpholinyl)-ethyl ester as a potential anti-inflammatory agent with improved aqueous solubility and metabolic stability

Although mollugin, the main ingredient of the oriental medicinal herb Rubia cordifolia, has considerable anti-inflammatory effects, it has poor aqueous solubility as well as poor metabolic and plasma stability. To overcome these shortfalls, various mollug

Mollugin derivatives, optical isomer thereof, or pharmaceutically acceptable salts thereof, and a pharmaceutical composition for preventing or treating inflammatory bowel disease comprising the same as an active ingredient

The present invention relates to mollugin derivatives, an optical isomer thereof, or pharmaceutically acceptable salts thereof, and a pharmaceutical composition for preventing or treating inflammatory bowel disease comprising the same as an active ingredient. The mollugin derivatives of the present invention become salts easily by introducing an amine group, so that a solubility improvement effect is remarkable compared to existing poorly-soluble substances, and in the case of treatment with the mollugin derivatives, the activity of inhibiting the adhesion of U937 cells, which are monocytic cells, in TNF-andalpha; or IL-6-inducible HT-29 cells was excellent, thereby being useful as pharmaceutical compositions for prevention or treatment of inflammatory bowel disease.(AA) Example 7 (10 andmu;M)(BB) Example 21 (10 andmu;M)COPYRIGHT KIPO 2017

Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin

Organocatalytic asymmetric epoxidation of chromenes mediated by iminium salt catalysts under non-aqueous conditions provided ees as high as 99%. Contrastingly, reaction under aqueous conditions can form the corresponding diol products with ees as high as 71%. The process has been used for the synthesis of the East African medicinal plant metabolite (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin.

New mollugin analogues and their antioxidant and antibacterial activities

The present invention relates to a new mollugin analogue and medical use thereof and, more specifically to newly synthesized mollugin analogues having both antibacterial and antioxidant activities, which can be effectively used as a medicine for oxidation-related diseases or as an antibacterial agent.

Facile synthesis of mollugin by kinetic control and anti-HCV (Hepatitis C Virus) activity of its analogues

Mollugin has been reported to have various biological activities including antineoplastic, antitumor, antiviral against the hepatitis B virus, anti-aging and antimutagenic activities. An effective and concise synthesis of mollugin in two steps including kinetic control from the cheap starting material 1,4-naphthoquinone has been introduced, and mollugin derivatives thus prepared are screened for their inhibition ability against the hepatitis C virus (HCV) and the dihydrobenzochromene structure might be an additional anti-HCV agent as a new leading compound.

Synthesis of the natural products 3-hydroxymollugin and 3-methoxymollugin

(Figure Presented) 3-Hydroxymollugin 2 and 3-methoxymollugin 3 are cytotoxic compounds isolated as minor compounds from Pentas longiflora and Rubia cordifolia. Syntheses of 3-hydroxymollugin 2 and 3-methoxymollugin 3 were developed starting from easily available 3-bromomollugin 6. Surprisingly, it was found that the reaction of 3-bromomollugin 6 with sodium methoxide in methanol resulted in the formation of 3-methoxymollugin 3 and the ring-contracted methyl isopropenylfuromollugin 7. A mechanism for this ring contraction is proposed on the basis of a pericyclic retro oxa-6π ring-opening reaction. A second synthesis of 3-hydroxymollugin 2 was based on epoxidation of methyl 3-(3-methylbut-2-enyl)-l,4-naphthoquinone-2-carboxylate 17 and subsequent reduction of the quinone moiety, ring transformation, and DDQ oxidation. The latter oxidation process results in 3-hydroxymollugin 2 along with the rearranged furomollugin 4, which is a ring-contracted analogue of the natural product mollugin 1.

Efficient one-pot trans-dihydroxylation of 2H-pyrans using dimethyldioxirane (DMD): synthesis of trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin natural products

An efficient one-pot formation of trans-diols on 2H-pyranyl rings was achieved by dimethyldioxirane in wet acetone. This new methodology was applied to the synthesis of natural products containing trans-diol on the pyranyl rings such as trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin.

A novel method for the synthesis of substituted benzochromenes by ethylenediamine diacetate-catalyzed cyclizations of naphthalenols to α,β-unsaturated aldehydes. Concise synthesis of the natural products lapachenole, dihydrolapachenole, and mollugin

A new synthetic route for biologically interesting benzochromenes was developed starting from naphthalenols and α,β-unsaturated aldehydes in the presence of ethylenediamine diacetate. This methodology was applied for the total synthesis of the biologicall