66346-59-6

Usage

Uses

Used in Pharmaceutical Industry:
5,7-Dihydroxy-4-propylcoumarin 98 is used as a precursor in the synthesis of new pharmaceutical compounds for its potential therapeutic applications and biological effects.
Used in Research Studies:
In the research industry, 5,7-Dihydroxy-4-propylcoumarin 98 is utilized to investigate its potential therapeutic applications and biological effects, contributing to the development of new medications and understanding of its properties.
Used in Anticoagulant Medications:
5,7-Dihydroxy-4-propylcoumarin 98 is employed as a key component in the development of anticoagulant medications, leveraging its anticoagulant properties to prevent blood clot formation and related health complications.

InChI:InChI=1/C12H12O4/c1-2-3-7-4-11(15)16-10-6-8(13)5-9(14)12(7)10/h4-6,13-14H,2-3H2,1H3

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 3249-68-1 ethyl butyroyl acetate 
• 6099-90-7 1,3,5-Trihydroxybenzene dihydrate 
• 30414-54-1 methyl 3-oxohexanoate 
• 101169-75-9 diacetoxy-5,7 propyl-4 coumarine 

Downstream Products

• 66346-55-2 5,7-dimethoxy-4-propyl-2H-1-benzopyran-2-one 
• 166983-58-0 5,7-Dihydroxy-8-propanoyl-4-propyl-2H-1-benzopyran-2-one 
• 303007-20-7 2-oxo-4-propyl-2H-chromene-5,7-diyl bis(4-methylbenzenesulfonate) 
• 5022-20-8 mammea B/BB 
• 1005322-84-8 5-hydroxy-8-phenyl-4-propyl-8,9-dihydro-2H,10H-pyrano[2,3-f]chromene-2,10-dione 
• 1005322-85-9 5-hydroxy-8-phenyl-4-propyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromene-2,6-dione 
• 1005322-86-0 5-hydroxy-8-(4-methylphenyl)-4-propyl-8,9-dihydro-2H,10H-pyrano[2,3-f]chromene-2,10-dione 
• 1604838-93-8 5-(4-fluorophenyl)-8-nitro-4-propyl-2H-furo[2,3-h]chromen-2-one 
• 1604838-91-6 5-(4-fluorobenzyloxy)-8-nitro-4-propyl-2H-furo[2,3-h]chromen-2-one 
• 1604838-58-5 5-hydroxy-2-phenyl-10-propyl-8-oxo-2H,8H-pyrano[2,3-f]chromen-6-carbaldehyde 
• 1604838-59-6 C₂₃H₁₇NO₆ 
• 142632-32-4 (+)-calanolide A 
• 161753-49-7 (+/-)-Calanolide D 

Relevant academic research and scientific papers

N-Oxide heterocycles and imidazoles replacing ring D of calanolides against Mycobacterium tuberculosis

We have explored the chemistry of N-oxide heterocycles and imidazoles replacing ring D of the natural product (+)-calanolide A, and have synthesized 12 new analogues, two of which were active against both R Mtb and NR Mtb with MIC values of 12.5 μg/mL, which would lead to further optimization for more potent anti-TB candidates.

Nano-BFn/cellulose: a bio-based nano-catalyst for synthesis of bio-active 7-hydroxycoumarins

Nano-BFn/cellulose as a modified bio-based nano-catalyst has been synthesized from nanocellulose and boron triflouride via very simple steps. This novel nano-catalyst exhibited many advantages in the synthesis of 7-hydroxycoumarins such as good

1-Nicotinoylbenzotriazole: A Convenient Tool for Site-Selective Protection of 5,7-Dihydroxycoumarins

1-Nicotinoylbenzotriazole (NicBt) was uncovered as an efficient protecting agent for the site-selective acylation of resorcinol-type phenolic groups with almost equal reactivity. The use of NicBt allows selective protection of the 7-OH group in 5,7-dihydr

FeCl3-catalysed ultrasonic-assisted, solvent-free synthesis of 4-substituted coumarins. A useful complement to the Pechmann reaction

The catalytic activity of FeCl3 for the synthesis of a variety of 4-substituted coumarins using high energy techniques has been investigated. The ultrasonic-assisted conditions provide a useful complement to the Pechmann reaction, affording the coumarin derivatives in excellent yields, under solvent-free conditions, in short reaction times using an inexpensive, mild and benign Lewis acid catalyst.

TETRIACYCLODIPYRANYL COUMARINS AND THE ANTI-HIV AND ANTI-TUBERCULOSIS USES THEREOF

The present invention relates to tctracyclodipyrano-coumarin compounds of general formula (I), wherein the substituents are defined herein. These compounds exihibit dual biological activities of anti human immunodeficiency virus type 1 (HIV-1) infection a

Scandium(III) triflate-catalyzed coumarin synthesis

Scandium(III) triflate is an excellent catalyst in the von Pechmann condensation. The solvent-free catalytic reactions proceed smoothly with a range of phenols and β-ketoesters in the presence of 10 mol% scandium(III) triflate at 80°C. This simple method affords various 4-substituted coumarins in good to excellent yield and is superior to the classical method in several aspects: solvent-free conditions, short reaction times, a decreased catalyst loading, a mild reaction temperature, and an easy workup. Copyright Taylor & Francis Group, LLC.

Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents

(+)-Calanolide A (1) as a natural product was previously found as an inhibitor of HIV-1 reverse transcriptase. In our further investigation of its template, racemic 11-demethyl-12-oxo calanolide A (15), which had two fewer chiral carbon centers at the C-11 and C-12 positions than (+)-calanolide A, had a comparably inhibitory activity and better therapeutic index (EC50 = 0.11 μM, TI = 818) against HIV-1 in vitro. A library based on its structural core was then designed and synthesized with introduction of nine diversity points in this article. The evaluations of anti-HIV-1 activity in vitro concluded their structure-activity relationships (SARs). A novel compound (10-bromomethyl-11-demethyl-12-oxo calanolide A, 123) was identified to have much higher inhibitory potency and therapeutic index (EC50 = 2.85 nM, TI > 10,526) than those of the class compound against HIV-1. This finding provided a very important clue that modifications of the C ring at the C-10 position may be conducted to obtain drug candidates with better activity against HIV-1.

Concise Synthesis of Anti-HIV-1 Active (+)-Inophyllum B and (+)-Calanolide A by Application of (-)-Quinine-Catalyzed Intramolecular Oxo-Michael Addition

(-)-Quinine-catalyzed intramolecular oxo-Michael addition (IMA) of 7-hydroxy-5-methoxy-8-tigloylcoumarins was developed for the enantioselective construction of 2,3-dimethyl-4-chromanone systems in the context of the asymmetric synthesis of anti-HIV-1 act

PROCESSES FOR PREPARING CALANOLIDE A AND INTERMEDIATES THEREOF

The present invention provides a production method of Calanolide A according to the following method wherein each symbol is as defined in the specification, as a more convenient and industrially practical method for the synthesis of Calanolide A from an easily available starting material.

Method for treating and preventing mycobacterium infections

Calanolides and analogues thereof that demonstrate potent mycobacterium activity are provided. Also provided is a method of using calanolides and analogues thereof for treating or preventing mycobacterium infections. The calanolides and analogues thereof provided are obtained via syntheses employing chromene 4 and chromanone 7 as key intermediates.