15679-28-4

Upstream product

• 65376-03-6 (3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one 
• 13149-04-7 (rac)-trans-4,5-bis(hydroxymethyl)cyclohex-1-ene 
• 108-05-4 vinyl acetate 
• 189683-61-2 dimenthyl trans-cyclohex-4-ene-1,2-dicarboxylate 
• 439919-46-7 cis-1,6-dihydroxymethyl-3-cyclohexene 
• 31139-02-3 (1S,2R)-2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 85-43-8 trans-4-Cylohexene-1,2-dicarboxylic anhydride 
• 17673-68-6 dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate 
• 88-98-2 trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 4841-85-4 trans-1,2-bis(ethoxycarbonyl)-4-cyclohexene 
• 4841-85-4 (1R,2R)-cyclohex-4-ene-1,2-dicarboxylic acid diethyl ester 
• 93603-11-3 1-methyl hydrogen 1,2-cis-1,2-cyclohex-4-ene dicarboxylate 
• 31139-02-3 (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid 

Downstream Products

• 173658-51-0 (1R,2R)-cyclohex-4-ene-1,2-dimethanol bis(methansulfonate) 
• 76155-27-6 (+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol 
• 56799-21-4 trans-6-Hydroxy-3-cyclohexen-1-carbaldehyd 
• 15679-27-3 (4S,5S)-4,5-bis(hydroxymethyl)cyclohexene 
• 82864-75-3 (1R,6R)-6-Hydroxymethyl-cyclohex-3-enecarboxylic acid 
• 3470-42-6 trans-8-oxabicyclo<4.3.0>non-3-ene 

Relevant academic research and scientific papers

Discovery of (E)-5,5-Difluoro-1-[2-[5-(3-fluorophenyl)pyridin-2-yl]vinyl]octahydrospiro(indene-2,5′-oxazolidin)-2′-one as a PAR1 Antagonist

In a previous study, we showed that several octahydroindene derivatives are potent protease activated receptor 1 (PAR1) antagonists. In the current study, we prepared a series of trans-fused 5,5-difulorooctahydroindenes which do not have a C5 stereogenic center, and evaluated their biological activities and metabolic stabilities. Compound 19 in this series, containing a spirooxazolidinone moiety at C2, showed excellent efficacy in both PAR1 binding (IC50 = 70 nM) and human platelet rich plasma (PRP) aggregation (IC50 = 0.19 μM), along with good metabolic stability (R50 = 345.8, 337.2, and 43.4 min in human, rat, and monkey liver microsomes, each), which is comparable to that of vorapaxar. Four stereoisomers of 19 were prepared and evaluated. (1S,2R,3aR,7aR)-5,5-Difluoro-1-[(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]vinyl]octahydrospiro(indene-2,5′-oxazolidin)-2′-one (31) was found to be the most active (IC50 = 21 nM) stereoisomer as PAR1 antagonist. Compound 31 exhibited good in vivo oral PK profiles and significant ex vivo antithrombotic efficacy in cynomolgus monkeys upon oral administration. When the plasma concentration of 31 was maintained above 200 ng/mL, platelet aggregation induced by haTRAP was completely inhibited.

Helical structures of bicyclic α-amino acid homochiral oligomers with the stereogenic centers at the side-chain fused-ring junctions

Chiral bicyclic α-amino acid (R,R)-Ab5,6=c with stereogenic centers at the γ-position of fused-ring junctions, and its enantiomer (S,S)-Ab5,6=c, were synthesized. The CD spectra of (R,R)-Ab5,6=c oligomers indicated that th

[6+5] FUSED BICYCLES AS A THROMBIN ANTAGONIST, PROCESS FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE BICYCLES

The present invention relates to the new [6+5] fused bicycle derivatives, pharmaceutically acceptable salts or isomers thereof, processes for preparing the same, and pharmaceutical compositions comprising the same. The [6+5] fused bicycle derivatives can antagonize the thrombin receptor and thus may be effectively used for the treatment and prevention of thrombus, platelet aggregation, atherosclerosis, restenosis, blood coagulation, hypertension, arrhythmia, angina pectoris, heart failure, inflammation and cancer when used alone or with other cardiovascular agents.

Synthesis and in vivo evaluation of 3,4-disubstituted gababutins

A range of 3,4-alkylated five-membered ring derivatives of gabapentin were synthesised. One compound (21) had an excellent level of potency against α2δ and was profiled in in vivo models of pain and anxiety.

INHIBITION OF BACTERIAL BIOFILMS WITH IMIDAZOLE DERIVATIVES

Disclosure is provided for imidazole derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

Asymmetric Diels-Alder reaction of 1,3-butadienes with (-)-dimenthyl fumarate in the presence of BBr3 and BBr3·OEt 2

Asymmetric synthesis of substituted cyclohexenes was performed by [4+2]-cycloaddition of (-)-dimenthyl fumarate to 1,3-butadienes in the presence of BBr3 and BBr3·OEt2. The latter are efficient catalysts for this reaction.

Total synthesis of the polyenoyltetramic acid polycephalin C

The total synthesis of the polyenoyltetramic acid polycephalin C is described. Key steps of the synthesis include a double Swern oxidation, double Takai reaction and a double Stille reaction. In addition, the absolute stereochemistry of the ring junction

Total synthesis of polycephalin C and determination of the absolute configurations at the 3′′,4′′ ring junction

Only through total synthesis could the absolute configuration of the 3′′R,4′′R ring junction of the polyenoltetramic acid polycephalin C (1) be unambiguously established. Key features of the synthesis include a double Swern oxidation, double Stille coupli

Complete relative stereochemistry of maitotoxin

By addressing the relative stereochemistry of the four acyclic portions via organic synthesis, the complete relative stereochemistry of maitotoxin (MTX) has been established as 1B. The relative stereochemistry of the C.1-C.15 portion was elucidated via a two-phase approach: (1) the synthesis of the eight diastereomers possible for model C, representing the C.1-C.11 portion, and the eight diastereomers possible for model D, representing the C.11-C.15 portion, and the comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 9 and 35 represent the relative stereochemistry of the corresponding portions of MTX; (2) the synthesis of the two remote diastereomers 51 and 52, and comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 51 represents the relative stereochemistry of the C.1-C.15 portion of MTX. The relative stereochemistry of the C.35-C.39, C.63-C.68, and C.134-C.142 acyclic portions was established via (1) the synthesis of the 8, 8, and 16 diastereomers possible for models E, F, and G, respectively, and (2) the comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 81, 117, and 187, respectively, represent the relative stereochemistry of the corresponding portions of MTX. Some biogenetic considerations have been given to speculate on the absolute configuration of MTX. The vicinal proton coupling constants observed for models 51, 81, 117, and 187 were used to elucidate their preferred solution conformation. Assembling the preferred solution conformations found for the four acyclic portions allows one to suggest that the approximate global conformation of MTX is represented by the shape of a hook, with the C.35-C.39 portion being its curvature. MTX appears to be conformationally relatively rigid, except for conformational flexibility around the C.7-C.9 and C.12-C.14 portions. On the basis of the experimental results gained in the current work, coupled with those in the AAL-toxin/fumonisin area, it has been pointed out that the structural properties of 51, 81, 117, 187 and their diastereomers are inherent to the specific stereochemical arrangement of the small substituents on the carbon backbone and are independent from the rest of the molecule. Thus, it has been suggested that each of these diastereomers has the capacity to install a unique structural characteristic through a specific stereochemical arrangement of substituents on the carbon backbone, and that fatty acids and related classes of compounds may be able to carry specific information and serve as functional materials in addition to structural materials.

Synthesis of enantiomerically pure bis(hydroxymethyl)-branched cyclohexenyl and cyclohexyl purines as potential inhibitors of HIV

The synthesis of the enantiomerically pure bis(hydroxymethyl)-branched cyclohexenyl and cyclohexyl purines is described. Racemic trans-4,5-bis(methoxycarbonyl)cyclohexene [(±)-6] was reduced with lithium aluminum hydride to give the racemic diol (±)-7. Resolution of (±)-7 via a transesterification process using lipase from Pseudomonas sp. (SAM-II) gave both diols in enantiomerically pure form. The enantiomerically pure diol (S,S)-7 was benzoylated and epoxidized to give the epoxide 9. Treatment of the epoxide 9 with trimethylsilyl trifluoromethanesulfonate and 1,5-diazabicyclo[5.4.0]undec-5-ene followed by dilute hydrochloric acid gave (1R,4S,5R)-4,5-bis[(benzoyloxy)methyl]1-hydroxycyclohex-2-ene (10). Acetylation of 10 gave (1R,4S,5R)-1-acetoxy-4,5-bis[(benzoyloxy)methyl]cyclohex-2-ene (11). (1R,4S,5R)-1-Acetoxy-4,5-bis[(benzoyloxy)methyl]cyclohex-2-ene (11) was converted to the adenine derivative 12 and guanine derivative 13 via palladium(0)-catalyzed coupling with adenine and 2-amino-6-chloropurine, respectively. Hydrogenation of 12 and 13 gave the corresponding saturated adenine derivative 14 and guanine derivative 15. (1R,4S,5R)-4,5-Bis[)benzoyloxy)methyl]-1-hydroxycyclohex-2-ene (10) was converted to the adenine derivative 16 and guanine derivative 17 via coupling with 6-chloropurine and 2-amino-6-chloropurine, respectively, using a modified Mitsunobu procedure. Hydrogenation of 16 and 17 gave the corresponding saturated adenine derivative 18 and guanine derivative 19. Compounds 12-19 were evaluated for activity against human immunodeficiency virus (HIV), but were found to be inactive. Further biological testings are underway.