4676-33-9

Upstream product

• 526-06-7 eudesmin 
• 4440-92-0 1,4-bis(3,4-dimethoxyphenyl),2,3-dimethylbutane-1,4-dione 
• 91-16-7 1,2-dimethoxybenzene 
• 4687-37-0 ethyl 3,4-dimethoxybenzoylacetate 
• 4687-40-5 diethyl 2,3-bis-(3,4-dimethoxybenzoyl)butane-1,4-dioate 
• 4687-44-9 2,5-bis-(3,4-dimethoxy-phenyl)-furan-3,4-dicarboxylic acid diethyl ester 
• 4687-31-4 2,5-bis-(3,4-dimethoxy-phenyl)-3,4-bis-hydroxymethyl-furan 
• 4440-92-0 (2S*,3S*)-1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane-1,4-dione 
• 1835-04-7 ethyl 3,4-dimethoxyphenyl ketone 
• 1835-05-8 2-bromo-1-(3,4-dimethoxyphenyl)propan-1-one 

Downstream Products

• 5701-82-6 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane 
• 24150-24-1 terameprocol 
• 528-63-2 all-cis-3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)tetrahydrofuran 

Relevant academic research and scientific papers

Synthesis of nordihydroguaiaretic acid derivatives and their bioactivities on S. pombe and K562 cell lines

Nordihydroguaiaretic acid (NDGA) and its synthetic analogues are potentially useful in treating diseases related to cancers, diabetes, viral and bacterial infections, and inflammation. In this paper, we report the optimal synthetic methods and the bioactivity study of terameprocol 2, NDGA derivative 3, and its cyclized analogue 4. The IC50 of these three compounds 2, 3 and 4 on the growth metabolism of Schizosacchromyces pombe and K562 cell lines were determined by microcalorimetry. The preliminary results showed that the compounds 2, 3 and 4 possessed good inhibition activities on S. pombe and K562 cell lines, and exhibited bidirectional biological effect and Hormesis effect. In particular, terameprocol 2 was found to possess the most potent inhibitory effect on K562 cell lines.

Structural modification of lignan compounds isolated from Nectandra species (Lauraceae)

In the genus Nectandra, the presence of certain types of secondary metabolites has been determined, including sesquiterpenes, phytosterols, polyalcohols, arylpropionic acid derivatives, flavonols, arylpropanoids, furofuran lignans, dihydrobenzofuran neolignans [1], and certain norlignans [2], alkaloids [3], tannins [4], diterpenes [5], and components of essential oils [6]. However, the chemotaxonomic characteristics are determined by the presence of lignan-type compounds [7]. The ultimate goal of structural modification of natural products is to obtain new drugs [8]. In that sense, there is a growing interest in lignans and their synthetic derivatives due to applications in cancer chemotherapy and various other pharmacological effects [9]. This work corresponds to the first report of this type of structural modification of lignan compounds (7,7′-epoxylignans and diaryldimethylbutane lignans) isolated from Nectandra species. Therefore, this work can be used as a starting point for structure-activity relationship studies.

SCALABLE SYNTHETIC PROCESS FOR MAKING TERAMEPROCOL

A manufacturing process for making terameprocol (1) which includes the following reaction scheme, wherein a first general reaction is the formation of a furan intermediate (39) and a second general reaction is the ring-reduction and ring-opening of the furan intermediate (39) to form the terameprocol (1)

A novel synthetic route to furan-lignans

Three naturally occurring furan-lignans and two analogs have been synthesized by a short and efficient route starting from the corresponding aryl acid. The selective reductive removal of allylic hydroxy by palladium oxide in a mixed solvent of THF-CHCl3 was employed as the key step.

Cyclization of Diketones to Pyridazine and Furan Derivatives

Condensation of (+/-)-2,3-bis(3,4-dimethoxybenzoyl)butane-1,4-dione 1 with different hydrazine bases afforded the corresponding pyridazines 2 and 3.Refluxing the diketone 1 with methanolic hydrogen chloride yielded the corresponding 3,4-dimethylfuran derivative 5.Reaction of acetonylacetone 6 with p-sulfamylphenylhydrazine afforded the corresponding 3,6-dimethyl-1H-pyridazine derivative 7.Reaction of 7 with the appropriate isocyanate and isothiocyanate yielded the corresponding benzenesulfonylurea 8 and thiourea 9 derivatives respectively.The structures of the compounds synthesized were affirmed by microanalyses and spectral studies.