75556-46-6

Upstream product

• 464-45-9 endo-borneol 
• 79-11-8 chloroacetic acid 
• 79-04-9 chloroacetyl chloride 
• 464-48-2 (1S)-camphor 

Downstream Products

• 20314-75-4 (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-morpholinoacetate 

Relevant academic research and scientific papers

Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process

In this study, we screened a large library of (+)-camphor and (?)-borneol derivatives to assess their filovirus entry inhibition activities using pseudotype systems. Structure-activity relationship studies revealed several compounds exhibiting submicromolar IC50 values. These compounds were evaluated for their effect against natural Ebola virus (EBOV) and Marburg virus. Compound 3b (As-358) exhibited the good antiviral potency (IC50 = 3.7 μM, SI = 118) against Marburg virus, while the hydrochloride salt of this compound 3b·HCl had a strong inhibitory effect against Ebola virus (IC50 = 9.1 μM, SI = 31) and good in vivo safety (LD50 > 1000 mg/kg). The results of molecular docking and in vitro mutagenesis analyses suggest that the synthesized compounds bind to the active binding site of EBOV glycoprotein similar to the known inhibitor toremifene.

Synthesis and in vitro study of novel borneol derivatives as potent inhibitors of the influenza A virus

Herein, we present the design and synthesis of a series of novel heterocyclic derivatives of (-)-borneol and (-)-isoborneol as potent inhibitors of the influenza A virus. All compounds were tested for their toxicity against MDCK cells and for virus-inhibiting activity against the influenza virus A/Puerto Rico/8/34 (H1N1). Compounds 7, 16 and 26 containing a morpholine fragment exhibited the highest efficiency as agents inhibiting the replication of the influenza virus A(H1N1) with selectivity indices of 82, 45 and 65, correspondingly. Derivatives 9 (SI = 23) and 18 (SI = 25) containing a 1-methylpiperazine motif showed moderate antiviral activity. Structure-activity analysis of this new series of borneol derivatives revealed that a 1,7,7-trimethylbicyclo[2.2.1]heptan scaffold is required for the antiviral activity.

Synthesis and biological activity of heterocyclic borneol derivatives

(figure presented) A series of novel heterocyclic derivatives of (–)-borneol has been prepared by the interaction of (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]-heptan-2-yl 2-chloroacetate and (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 3-chloropropanoate with different N- and S-nucleophiles. The obtained products were screened for antiviral, antiulcer, and analgesic activity.

S-Substituted-2-mercaptobenzthiazolium-based chiral ionic liquids: efficient organocatalysts for enantioselective sodium borohydride reductions of prochiral ketones

Novel chiral ionic liquids having chirality in their cationic part have been synthesized for evaluation of their catalytic potential as organocatalysts in sodium borohydride reduction of prochiral ketones to yield optically active secondary alcohols. The chiral ionic liquids have been synthesized from the reaction of (?)-menthol or (?)-borneol, chloroacetic acid and S-methyl/benzyl-2-mercaptobenzthiazole. The synthesized chiral ionic liquids have been characterized by 1H, 13C NMR and Mass spectrometry. Moderate to excellent enantiomeric excess (ee?>?99%) has been obtained in asymmetric sodium borohydride reduction of prochiral ketones using these salts as chiral catalysts.

New benzimidazolium-based chiral ionic liquids: Synthesis and application in enantioselective sodium borohydride reductions in water

New chiral ionic liquids based on benzimidazolium salts have been synthesized from the reaction of (-)-menthol or (-)-borneol, chloroacetic acid and 1-methylbenzimidazole. The structures of these chiral ionic liquids have been confirmed from 1H

Stereoselective oxidation of methyl phenyl sulfide in the presence of chiral ionic liquids

Several ionic liquids containing a chiral center either in the cation or in the anion have been prepared. They have been applied as catalysts and solvents for stereoselective oxidation of methyl phenyl sulfide to obtain the respective sulfoxide.

Asymmetric diastereoselective thia-hetero-Diels-Alder reactions of dithioesters

Asymmetric thia-Diels-Alder reactions involving new dithioesters bearing a chiral auxiliary are described, with diastereoselectivities up to 78%. Double-stereodifferentiating experiments employing chiral substrates in the presence of a chiral Lewis acid c

SUCCINIC ACID DIESTER DERIVATIVE, PROCESS FOR PRODUCTION THEREOF, AND USE OF THE DERIVATIVE IN THE PRODUCTION OF PHARMACEUTICAL PREPARATION

The present invention provides with a process of preparing an optically active succinimide derivative, which is a key intermediate for production of ranirestat. A compound (3) is easily prepared by treating the derivative of succinic acid diester of the formula (2): wherein R1 is an amino group protected with a group removed by hydrogenolysis or a tert-butoxycarbonylamino group and R2 is an ethyl group optionally substituted with one or two methyl group(s) at α-position, provided that R2 is not a tert-butyl group when R1 is a tert-butoxycarbonylamino group; with alkali metal alkoxide and the compound (3) can be an important intermediate for production of ranirestat.

Synthesis of new chiral ionic liquids based on (-)-menthol and (-)-borneol

New chiral ionic liquids (CILs) based on (-)-menthol and (-)-borneol were designed and synthesized in very good yields using a simple and efficient 3-step strategy. The properties and characterization of these compounds are discussed.