6071-93-8

Upstream product

• 102449-34-3 4-diphenylmethylene-1-piperidinecarboxylic acid ethyl ester 
• 591-51-5 phenyllithium 
• 1690-75-1 1-methyl-piperidine-4-carboxylic acid methyl ester 
• 119-61-9 benzophenone 
• 29976-53-2 N-ethoxycarbonyl-4-piperidone 
• 5570-77-4 4-chloro-1-methylpiperidine 
• 6071-92-7 VUF 4589 

Downstream Products

• 100169-94-6 1,1-dimethyl-4-(diphenylmethylene)piperidinium iodide 
• 688304-93-0 6-(4-Benzhydrylidene-piperidin-1-yl)-hexanoic acid methyl ester 
• 137406-19-0 5-(4-Benzhydrylidene-piperidin-1-yl)-pentanoic acid ethyl ester 
• 137406-18-9 4-(4-Benzhydrylidene-piperidin-1-yl)-butyric acid ethyl ester 
• 137406-16-7 3-(4-Benzhydrylidene-piperidin-1-yl)-propionic acid ethyl ester 
• 167108-56-7 (4-Benzhydrylidene-piperidin-1-yl)-acetic acid ethyl ester 
• 50706-57-5 4-(diphenylmethylene)piperidine 
• 102449-34-3 4-diphenylmethylene-1-piperidinecarboxylic acid ethyl ester 
• 5704-22-3 4-(diphenylmethyl)-1-methylpiperidine 

Relevant academic research and scientific papers

Steric structure–activity relationship of cyproheptadine derivatives as inhibitors of histone methyltransferase Set7/9

Set7/9 is a histone lysine methyltransferase, but it is also thought to be involved in a wide variety of pathophysiological functions. We previously identified cyproheptadine, which has a characteristic butterfly-like molecular conformation with bent tricyclic dibenzosuberene and chair-form N-methylpiperidine moieties, as a Set7/9 inhibitor. In this work, we synthesized several derivatives in order to examine the steric structure–inhibitory activity relationship. We found that even a small change of molecular shape due to reduction or replacement of the 10,11-olefinic bond of the tricyclic ring generally resulted in a drastic decrease of the inhibitory activity. Our results should be useful not only for development of more potent and selective inhibitors, but also for the construction of novel inhibitor scaffolds.

Treatment of CNS disorders using CNS target modulators

The invention is directed to compositions and methods useful for treating Central Nervous System (CNS) disorders. Furthermore, the invention provides compositions and methods of treating sleep disorders. More specifically, the invention is directed to the compositions and use of derivatized, histamine antagonists for the treatment of sleep disorders.

TREATMENT OF CNS DISORDERS USING CNS TARGET MODULATORS

The invention is directed to compositions used for treating Central Nervous System (CNS) disorders. In addition, the invention provides convenient methods of treatment of a CNS disorder. Furthermore, the invention provides methods of treating sleep disorders using compositions that remain active for a discrete period of time to reduce side effects. More specifically, the invention is directed to the compositions and use of derivatized, e.g., ester or carboxylic acid derivatized, antihistamine antagonists for the treatment of sleep disorders.

Synthesis, affinity at 5-HT(2A), 5-HT(2B) and 5-HT(2C) serotonin receptors and structure-activity relationships of a series of cyproheptadine analogues

Cyproheptadine is a drug that shows high affinity for type 2 (5-HT2) receptors. We studied a series of compounds obtained by modification of the tricyclic system of Cyp (dibenzocycloheptadiene): 2f (thioxanthene), 2g (xanthene), 2h (dihydrodibenzocycloheptadiene), 2j (diphenyl), 2i (fluorene), and 3b (phenylmethyl). Their activities at the rat cerebral cortex 5-HT(2A) receptor were (pK(i) ± S.E.M.): 8.80 ± 0.11 (Cyp), 8.60 ± 0.07 (2f), 8.40 ± 0.02 (2g), 8.05 ± 0.03 (2h), 7.87 ± 0.12 (2j), 6.70±0.02 (2i) and 6.45±0.02 (3b); those at the rat stomach fundus 5-HT(2B) receptor (pA2±S.E.M.) were: 9.14±0.25 (Cyp), 8.49±0.07 (2F), 7.58±0.58 (2g), 7.02±0.14 (2h), 6.07±0.20 (2j), and undetectable (21, 3b); and those at the pig choroidal plexus 5-HT(2C) receptor (pK(i)±S.E.M.) were: 8.71 ± 0.08 (Cyp), 8.68 ± 0.01 (20, 8.58 ± 0.20 (2g), 7.95 ± 0.05 (2h), 7.57 ± 0.04 (2j), 6.98 ± 0.04 (2i) and 6.63 ± 0.20 (3b). The slopes did not differ significantly from unity. The compounds exhibited the same order of activities at every type of receptor, and the most active molecules presented certain steric (butterfly conformation of the tricyclic system) and electrostatic (proton affinity on the top of the central rings) patterns. It is concluded that the activity of cyproheptadine derivatives at 5-HT2 receptors is related to these molecular features, which make feasible a common disposition to interact with all three 5-HT2 subtypes.

Structure-activity relationship of newly synthesized quinoline derivatives for reversal of multidrug resistance in cancer

The effect of 24 newly synthesized quinoline derivatives on tumor cell multidrug resistance (MDR) was examined in vitro. At low concentrations, these compounds enhanced the accumulation of [3H]vincristine in K562/ADM cells and reversed tumor cell MDR. The results of the structure-activity relationship analysis indicate that in highly active compounds the two aryl rings in the hydrophobic moiety deviate from a common plane, so they are capable of interacting with hydrogen bond donors of P-170 glycoprotein (P- gp) via π-hydrogen-π interactions. Other major structural features which influence the MDR-reversing activities of these compounds are a quinoline nitrogen atom and a basic nitrogen atom in piperazine. Furthermore, in highly active compounds, the distance between the hydrophobic moiety and the basic nitrogen atom (an atom connected to 2-hydroxypropoxyquinoline) must be at least 5 A?. Several compounds were found to reverse vincristine resistance in K562/ADM cells in vitro, and compound 16 (MS-209) was selected for clinical studies.

Cyproheptadine analogues: Synthesis, antiserotoninergic activity, and structure-activity relationships

A series of cyproheptadine related compounds was synthesized and tested pharmacologically. In comparison with cyproheptadine, these compounds do not have a central ring and some contain groups other than N-methyl. Synthesis was carried out with low-valent

UNUSUAL REDUCTIONS INDUCED BY FORMIC ACID

Treatment of xanthene carbinol 1a or xanthenylidene derivative 2a with refluxing formic acid unexpectedly gave dihydro compound 3a.Thioxanthene and acridine carbinols 1b and 1c and acridinylidene derivative 2c were also partially reduced when treated with formic acid.