114892-46-5

Upstream product

• 75-07-0 acetaldehyde 
• 535-11-5 Ethyl 2-bromopropionate 
• 34293-67-9 methyl 3-(R)-hydroxy-2-(S)-methylbutanoate 
• 1253963-45-9 methyl 3S,11S-dihydroxytetradecanoate 11-O-α-L-rhamnopyranosyl-(1->3)-O-[4-O-2R-methyl-3R-O-(2R-methyl-3R-hydroxybutyryl)butyryl]-β-D-quinovopyranosyl-(1->4)-O-(2-O-2S-methylbutyryl)-α-L-rhamnopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->2)-[O-(4-O-2S-methyl-3S-hydroxybutyryl)-α-L-rhamnopyranosyl-(1->6)]-β-D-glucopyranoside 
• 1253963-47-1 methyl 3S,11S-dihydroxytetradecanoate 11-O-β-D-quinovopyranosyl-(1->4)-O-(2-O-2S-methylbutyryl)-α-L-rhamnopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->2)-{[4-O-2R-methyl-3R-O-(2R-methyl-3R-hydroxybutyryl)butyryl]-O-α-L-rhamnopyranosyl-(1->6)}-β-D-glucopyranoside 
• 1584164-96-4 C₄₆H₇₉NO₁₈ 
• 1584164-98-6 C₈₇H₁₄₉NO₄₀ 
• 1584164-99-7 C₈₉H₁₅₃NO₄₀ 
• 1584165-00-3 C₈₇H₁₄₉NO₃₉ 
• 1584165-01-4 C₈₆H₁₄₇NO₃₉ 
• 1584165-02-5 C₈₈H₁₅₁NO₃₉ 
• 90033-09-3 N-(2-t-butyldimethylsiloxyethyl)-2-methylacetoacetamide 
• 80-59-1 Tiglic acid 
• 27372-03-8 ethyl 3-hydroxy-2-methylbutyrate 

Downstream Products

• 80-59-1 Tiglic acid 
• 7732-18-5 water 

Relevant academic research and scientific papers

Resin Glycosides from Ipomoea alba Seeds as Potential Chemosensitizers in Breast Carcinoma Cells

Multidrug resistance is the expression of one or more efflux pumps, such as P-glycoprotein, and is a major obstacle in cancer therapy. The use of new potent and noncytotoxic efflux pump modulators, coadministered with antineoplastic agents, is an alternative approach for increasing the success rate of therapy regimes with different drug combinations. This report describes the isolation and structure elucidation of six new resin glycosides from moon vine seeds (Ipomoea alba) as potential mammalian multidrug-resistance-modifying agents. Albinosides IV-IX (1-6), along with the known albinosides I-III (7-9), were purified from the CHCl3-soluble extract. Degradative chemical reactions in combination with NMR spectroscopy and mass spectrometry were used for their structural elucidation. Four new glycosidic acids, albinosinic acids D-G (10-13), were released by saponification of natural products 3-6. They were characterized as tetrasaccharides of either convolvulinolic (11S-hydroxytetradecanoic) or jalapinolic (11S-hydroxyhexadecanoic) acids. The potentiation of vinblastine susceptibility in multidrug-resistant human breast carcinoma cells of albinosides 1-6 was evaluated by modulation assays. The noncytotoxic albinosides VII (4) and VIII (5), at a concentration of 25 μg/mL, exerted the strongest potentiation of vinblastine susceptibility, with a reversal factor (RFMCF-7/Vin+) of 201- and >2517-fold, respectively.

Acylated glycosides of hydroxy fatty acid methyl esters generated from the crude resin glycoside (pharbitin) of seeds of pharbitis nil by treatment with indium(III) chloride in methanol

Treatment of the crude ether-insoluble resin glycoside (convolvulin) from seeds of Pharbitis nil (Pharbitis Semen), called pharbitin, with indium(III) chloride in methanol provided seven oligoglycosides of hydroxy fatty acid methyl esters partially acylated by 2-methyl-3-hydroxybutyric (nilic) and 2S-methylbutyric acids. Their structures were elucidated on the basis of NMR and MS data and chemical conversions.

Calyhedins I–VI: Resin glycosides from the rhizomes of Calystegia hederacea

Six previously undescribed resin glycosides, calyhedins I–VI, were isolated from the rhizomes of Calystegia hederacea Wall., which are the first genuine resin glycosides isolated from C. hederacea. The structures of calyhedins I–VI were determined based on spectroscopic data and chemical evidence. All the compounds have macrolactone structures (jalapins), and their sugar moieties were partially acylated by five organic acids. Calyhedins I, II–V, and VI have 27-, 28-, and 23-membered rings, respectively, and calyhedins IV–VI are the first jalapins with a sugar chain consisting of seven monosaccharides. Additionally, the cytotoxic activity of calyhedins II and III toward HL-60 human promyelocytic leukemia cells was evaluated. Both compounds demonstrated almost the same activity as the positive control, cisplatin.

Unusual ether-type resin glycoside dimers from the seeds of Cuscuta chinensis

Two new resin glycosides, cuses 3 (1) and 4 (2), were initially obtained from the seeds of Cuscuta chinensis. Both of them contained a reducing glucose unit, and thus existed as a pair of isomers. In order to solve the existing problem of tautomerism, the remanent resin glycoside fraction was converted into aminoalditol derivatives with p-anisidine, and then another eight new resin glycosides cuses 5-12 (3-10) were further isolated. Cuses 7-12 (6-10) were considered to be generated via glycosidation of two acylated oligosaccharides, and thus characterized as ether-type resin glycoside dimers. Their structures including absolute stereochemistry were elucidated by a combination of spectroscopic and chemical methods. Compounds 3-10 exhibited cytotoxic activity toward MCF-7, SMMC-7721, and MG-63 cell lines with IC50 values ranging from 8.72 to 59.35 μg/mL.

Three acylated glycosidic acid methyl esters and two acylated methyl glycosides generated from the convolvulin fraction of seeds of Quamoclit pennata by treatment with indium(III) chloride in methanol

Treatment of the ether-insoluble resin glycoside (convolvulin) fraction from seedsof Quamoclit pennata (Convolvulaceae) with indium(III) chloride in methanol provided three oligoglycosides of hydroxy fatty acid (glycosidic acid) methyl esters and two methyl glycosides, which were partially acylated by a glycosidic acid, 75-hydroxydecanoic acid 7-0-β-d-quinovopyranoside (quamoclinic acid B) and/or two organic acids, (E)-2-methylbut-2-enoic (tiglic) acid and/or 3R-hydroxy-2R-methylbutyric (nilic) acid. Theirstructures were elucidated on the basis of spectroscopic data and chemical conversions.

Mammalian multidrug resistance lipopentasaccharide inhibitors from Ipomoea alba seeds

As part of an ongoing project to identify inhibitors of multidrug efflux pumps, three new resin glycosides, albinosides I-III (1-3), were isolated from a CHCl3-soluble extract from the seeds of moon vine (Ipomoea alba). Their structures were established through NMR spectroscopy and mass spectrometry as partially acylated branched pentasaccharides derived from three new glycosidic acids, named albinosinic acids A-C (4-6). The same oligosaccharide core formed by two d-quinovose, one d-glucose, and two l-rhamnose units was linked to either convolvulinolic or jalapinolic acid for 1 and 3, respectively. They were partially esterified with (2R,3R)-3-hydroxy-2-methylbutanoic, acetic, or 2-methyl-2-butenoic acid. Compound 2 has two d-quinovose and three l-rhamnose units, linked to convolvulinolic acid, and its esterifying residues were characterized as two units of 2-methyl-2-butenoic acid. The aglycone lactonization site was located at C-2 of the terminal rhamnose unit (Rha) for 1, at C-3 of the terminal rhamnose unit (Rha') for 2, and at C-3 of the second saccharide unit (Glc) for 3. Reversal of multidrug resistance by this class of plant metabolites was also evaluated in vinblastine-resistant human breast carcinoma cells (MCF-7/Vin). The noncytotoxic compound 3 exerted the strongest potentiation effect of vinblastine susceptibility to over 2140-fold, while a moderate activity was observed for 1 (3.1-fold) and 2 (2.6-fold) at a concentration of 25 μg/mL.

Glycolipid ester-type heterodimers from Ipomoea tyrianthina and their pharmacological activity

Tyrianthins A (1) and B (2), two new partially acylated glycolipid ester-type heterodimers were isolated from Ipomoea tyrianthina. Scammonic acid A was determined as the glycosidic acid in both monomeric units. Tyrianthin A (1) (IC50 0.24 ± 0.0

Novel coumarin and chromene compounds and methods of preparation and use thereof for treating or preventing viral infections

The present invention relates to methods of preparation and use of coumarin and chromene compounds for treating or preventing viral infections.

Methods for preparing antiviral calanolide compounds

The present invention relates to methods for preparing 2,2-dimethyl-5-acyloxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (5) and 2,2-dimethyl-5-hydroxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (6) and their use as intermediates for the synthesis of antiviral calanolide compounds. For example, Fries rearrangement on compound 5 or Friedel-Crafts reaction on 6, yields intermediate 2,2-dimethyl-5-hydroxy-6-propionyl-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (4), which, in turn, can be converted to (+)-calanolide A and (?)-calanolide B. The coupling of compound 6 with the appropriate chiral molecule under Mitsunobu or nucleophilic displacement leads to the asymmetric synthesis of antiviral calanolide compounds.

Methods for preparing antiviral calanolide compounds

The present invention relates to methods for preparing 2,2-dimethyl-5-acyloxy-10-propyl-2H,8H-benzo[ 1,2-b:3,4-b ′]dipyran-8-one (5) and 2,2-dimethyl-5-hydroxy- 10-propyl-2H,8H-benzo[1,2-b:3,4-b ′]dipyran-8-one (6) and their use as intermediates for the synthesis of antiviral calanolide compounds. For example, Fries rearrangement on compound 5 or Friedel-Crafts reaction on 6, yields intermediate 2,2-dimethyl-5-hydroxy-6-propionyl-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (4), which, in turn, can be converted to (+)-calanolide A and (?)-calanolide B. The coupling of compound 6 with the appropriate chiral molecule under Mitsunobu or nucleophilic displacement leads to the asymmetric synthesis of antiviral calanolide compounds.