221666-27-9

Usage

Uses

Used in Pharmaceutical Industry:
CONOCARPAN is used as a potential therapeutic agent for its antimicrobial, antitumor, and antiplasmodial properties. Its diverse biological activities make it a candidate for the development of new drugs to combat various diseases and infections.
Used in Antimicrobial Applications:
CONOCARPAN is used as an antimicrobial agent to target and inhibit the growth of harmful microorganisms, such as bacteria and fungi. Its effectiveness in this application could lead to the development of new treatments for infections and diseases caused by these pathogens.
Used in Antitumor Applications:
CONOCARPAN is used as an antitumor agent, potentially inhibiting the growth and proliferation of cancer cells. Its ability to target tumor cells could contribute to the development of novel cancer therapies and improve patient outcomes.
Used in Antiplasmodial Applications:
CONOCARPAN is used as an antiplasmodial agent, targeting the Plasmodium parasites responsible for malaria. Its effectiveness in this application could lead to the development of new treatments for this life-threatening disease, particularly in regions where malaria is prevalent.
Used in Drug Delivery Systems:
To enhance the efficacy and bioavailability of CONOCARPAN, researchers are exploring the use of drug delivery systems, such as organic and metallic nanoparticles, as carriers. These systems aim to improve the delivery of CONOCARPAN to target cells, increasing its therapeutic potential and reducing potential side effects.

Upstream product

• 944249-92-7 toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester 
• 944249-89-2 toluene-4-sulfonic acid 4-[(R)-1-(4-formyl-2-iodophenoxy)allyl]phenyl ester 
• 944249-90-5 toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester 
• 944249-84-7 (2E)-3-[4-(toluene-4-sulfonyloxy)phenyl]-2-propenoic acid ethyl ester 
• 944249-85-8 toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester 
• 944249-86-9 toluene-4-sulfonic acid 4-[(2S,3R)-3-hydroxymethyloxyranyl]phenyl ester 
• 824-94-2 p-methoxybenzyl chloride 
• 1158723-06-8 (2R,3S)-3-methyl-5-[(E)-propen-1-yl]-2-(4-triisopropylsilyloxyphenyl)-2,3-dihydrobenzofuran 
• 6336-44-3 (E)-propenylboronic acid 
• 519164-56-8 1-(5-bromo-2-((4-methoxybenzyl)oxy)phenyl)ethanone 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 1426659-07-5 C₁₅H₁₂BrFO₂ 
• 1346146-33-5 (5-bromo-2-fluoro-phenyl)-acetyl chloride 
• 883514-21-4 2-(5-bromo-2-fluoro-phenyl)acetic acid 

Downstream Products

• 130659-24-4 C₃₆H₃₆O₄ 
• 130659-24-4 C₃₆H₃₆O₄ 

Relevant academic research and scientific papers

First synthesis of naturally occurring (±)-epi-conocarpan

(±)-epi-Conocarpan 1 was synthesized via the key intermediate 5-bromo-cis-2-(4-methoxyphenyl)-3-methyl-2,3-dihydrobenzofuran 6 which was synthesized by a ruthenium(II) porphyrin-catalyzed intramolecular C-H insertion reaction using aryl tosylhydrazone salt 5 as the carbene source, starting from the commercially available 5-bromo-2-hydroxyacetophenone.

Enantioselective Oxy-Heck–Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (?)-Conocarpan

This work discloses the first examples of an effective enantioselective oxy-Heck–Matsuda reaction using a variety of styrenic olefins to generate chiral dihydrobenzofurans. The reaction proceeds in moderate to good yields, with high trans diastereoselectivity (up to 20:1) in enantioselectivities up to 90:10 using the N,N-ligand pyrimidine-bisoxazoline (PyriBox). The oxy-Heck–Matsuda reactions were carried out under mild conditions and rather low catalyst loadings. The feasibility and practicality of the process is demonstrated by a concise total synthesis of the neolignan (?)-conocarpan. X-ray diffraction of an advanced brominated intermediate in the route to (?)-conocarpan has allowed the unequivocal assignment of the absolute stereochemistry of the oxy-Heck–Matsuda aryldihydrobenzofuran products. A rationale for the mechanism operating in these enantioselective oxy-Heck–Matsuda reactions is also presented. (Figure presented.).

Concise asymmetric synthesis of (+)-conocarpan and obtusafuran

The asymmetric synthesis of three natural products: (+)-conocarpan, both (+)- and (-)- obtusafuran is disclosed. The highlights of the synthesis are the enantioselective hydrogenation of prochiral ketones via dynamic kinetic resolution to afford chiral alcohols. Intramolecular ring closure via either Sr reaction or metal-catalyzed C-O bond formation led to the construction of the trans-dihydrobenzofuran core. Georg Thieme Verlag Stuttgart · New York.

Cerium ammonium nitrate-mediated the oxidative dimerization of p-alkenylphenols: A new synthesis of substituted (±)-trans- dihydrobenzofurans

A new method for the preparation of substituted dihydrobenzofurans is described. The p-alkenylphenols, mediated by cerium ammonium nitrate (CAN), undergo the oxidative dimerization to generate substituted dihydrobenzofurans including (±)-conocarpan, (±)-licarin A, (±)-acuminatin, as well as their related substituted dihydrobenzofurans.

Asymmetric synthesis of neolignans (-)-epi-Conocarpan and (+)-Conocarpan via Rh(II)-catalyzed C-H insertion process and revision of the absolute configuration of (-)-epi-Conocarpan

(Chemical Equation Presented) Catalytic asymmetric synthesis of neolignan natural products (-)-epi-conocarpan and (+)-conocarpan has been achieved by exploiting an enantio- and diastereoselective intramolecular C-H insertion reaction to construct a cis-2-

Synthesis of (-)-conocarpan by two routes based on radical cyclization and establishment of its absolute configuration

Two independent routes for the total synthesis of the bioactive neolignan (-)-conocarpan are described. The first (98% ee) is based on formal radical cyclization onto a benzene ring, and involves a 5-exo-trigonal closure onto a double bond restrained within a 6-membered ring. The second route (88% ee), which is shorter, is based on 5-exo-trigonal cyclization of an aryl radical onto a pendant terminal double bond. The two routes differ in their degree of stereoselectivity. The absolute configuration originally assigned to (+)-conocarpan had previously been called into question on the basis of empirical chiroptical rules; the present chemical work confirms the need for revision, and the assigned absolute configurations of several compounds correlated with (+)-conocarpan must also be changed. The Royal Society of Chemistry.

Total synthesis of (-)-conocarpan and assignment of the absolute configuration by chemical methods

(-)-Conocarpan (1) was synthesized by a method based on radical cyclization, and the absolute configuration was established by chemical degradation; the original 2R,3R-assignment to (+)-conocarpan should be reversed, as suggested by a later chiroptical study of model 2,3-dihydrobenzofurans. The Royal Society of Chemistry.

Synthesis of 2,3-dihydrobenzofurans by Mn(OAc)3-based oxidative cycloaddition of 2-cyclohexenones with alkenes. Synthesis of (±)-conocarpan

Oxidative cycloaddition of a 2-cyclohexenone or α-tetralone and an alkene with dried Mn(OAc)3 in benzene at 80-140 °C provides a general route to dihydrobenzofurans 15 and dihydronaphthofurans 17. Although the yields are modest, this one-pot reaction provides simple access to these compounds, which have previously been prepared by multistep routes. Oxidative cycloaddition of 2-cyclohexenones with β-methylstyrenes provides a new route to benzofuranoid neolignans, which was applied to the synthesis of conocarpan (22). The formation of 2-acetoxyhexanedioic acids 27 and 47 from acetoxylation of 2-cyclohexenones in HOAc, but not in benzene, opens up a new class of Mn(OAc)3 reactions and explains Watt and Demir's discovery that much higher yields of α'-acetoxy enones are obtained in benzene than in HOAc.