538-09-0Relevant articles and documents
Nortropine alcohol salting-out preparation method
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Paragraph 0032; 0034-0036; 0038-0040; 0042-0044; 0046-0047, (2020/07/21)
The invention provides a nortropine alcohol salting-out preparation method, which comprises the following steps: by taking N-ethoxycarbonyl methyltropone as a raw material, carrying out Raney nickel catalytic hydrogenation, hydrolysis, salting-out and refining to finally obtain nortropine alcohol with the purity of more than 99%. The method has the following advantages: 1, the catalytic hydrogenation temperature of Raney nickel is relatively low (20-100 DEG C), and the pressure is 0.5-1MPa; 2, the tedious operation of extracting for 7-10 times by using chloroform is omitted, the use of a solvent is saved, and the pollution is reduced; and 3, the product quality is greatly improved, and the crude product can reach 98% or above.
Enhanced antibacterial activity of endo-nortropine substituted (C-7) fluoroquinolones against V. cholerae, S. aureus and B. subtilis
Salunke, Ramkrushna Ashok,Sidhu, Chandni,Kumar, Ashok,Pinnaka, Anil Kumar,Bansal, Baldev Raj,Chhibber, Manmohan
, p. 895 - 904 (2018/09/10)
Introduction: Bacterial infections account for maximum deaths worldwide than for any other single cause. Methods: Here in, we report a convenient synthesis of new fluoroquinolone molecules substituted with endo-nortropine and its derivatives at C-7position. All the synthesized molecules, when screened for their antibacterial activity by agar diffusion method against Vibrio cholerae, Bacillus subtilis, Staphylococcus aureus and Escherichia coli were found to be active against the first three strains. The shortlisted compounds in the series, RG and RO, were further evaluated to determine their MIC values by micro-dilution broth assay. Result & Conclusion: Compound RG was ten times more effective in case of S. aureus (15.0 nM), two times in case of V. cholerae (3.7 nM) and the same as that of standard drug Levofloxacin in case of Bacillus subtilis (7.8 nM). Compound RO also displayed an impressive MIC value (62.5 nM) in case of S. aureus as compared to control (125 nM). The results have been supported by in-silico docking studies, where increased hydrogen bonding interactions in case of RG as compared to standard drug levofloxacin with DNA gyrase (2XCT) of S. aureus resulted in decreased energy of the former.
A METHOD FOR THE N-DEMETHYLATION OF N-METHYL HETEROCYCLES
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Page/Page column 42, (2011/04/19)
The present invention provides methods of N-demethylating, N-methylated heterocycles and N-methyl, N-oxide heterocycles using a transition metal with an oxidation state of zero, ferrocene or substituted derivatives thereof, or Cr 3+ .N-demethylated heterocycles prepared by the methods of the present invention are also provided.
N-Demethylation of N-methyl alkaloids with ferrocene
Kok, Gaik B.,Scammells, Peter J.
supporting information; experimental part, p. 4499 - 4502 (2010/09/15)
Under Polonovski-type conditions, ferrocene has been found to be a convenient and efficient catalyst for the N-demethylation of a number of N-methyl alkaloids such as opiates and tropanes. By judicious choice of solvent, good yields have been obtained for dextromethorphan, codeine methyl ether, and thebaine. The current methodology is also successful for the N-demethylation of morphine, oripavine, and tropane alkaloids, producing the corresponding N-nor compounds in reasonable yields. Key pharmaceutical intermediates such oxycodone and oxymorphone are also readily N-demethylated using this approach.
2,6-Disubstituted piperiddines as modulators
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Page/Page column 22, (2010/11/28)
The present invention is further directed to compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R16, R17, R18, R19, R20, R21 and R22 are as defined herein) which are modulators of chemokine receptor activity and are useful in the prevention or treatment of certain inflammatory and immunoregulatory disorders and diseases, allergic diseases, atopic conditions including allergic rhinitis, dermatitis, conjunctivitis, and asthma, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which chemokine receptors are involved.
Alkaloids of Convolvulus subhirsutus from Uzbekistan
Gapparov,Razzakov,Aripova
, p. 291 - 292 (2008/03/15)
Convolvine, convolamine, convolidine, phyllalbine, and the new alkaloid phyllalbine N-oxide and the aminoalcohol nortropine were isolated from the total alkaloids of Convolvulus subhirsutus and for the first time from this plant.
Combinatorial synthesis of benztropine libraries and their evaluation as monoamine transporter inhibitors
Pedersen, Hanne,Sinning, Steffen,Buelow, Anne,Wiborg, Ove,Falborg, Lise,Bols, Mikael
, p. 2861 - 2869 (2007/10/03)
A combinatorial synthesis of benztropine analogues is presented. Radical azidonation of 3-benzyloxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 3 to 3-(1-azidobenzyloxy)-8-azabicyclo[3.2.1]octane-8- carboxylic acid terf-butyl ester 4 was used as a key step in the synthesis. This step was optimized by adding 10% DMF to the reaction. Reaction of 4 with phenyl magnesium bromide followed by Boc removal and N-methylation gave benztropine 1. Reaction of five-component Grignard reagents with 4 was used to create a two-dimensional library of 25 N-normethylbenztropine analogues. Further reaction of this library with five alkyl bromides was carried out to create a three-dimensional library containing 125 compounds. Screening of the libraries towards binding and inhibition of uptake of the human dopamine (hDAT), serotonin (hSERT) and norepinephrine transporters (hNET) was carried out. None of the synthesized compounds were found to be stronger than benztropine, and none were selective for inhibition of binding over monoamine uptake.
Substituted benzothiazole amide derivatives
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, (2008/06/13)
A compound of formula I and a method of treatment of diseases, related to modulation of the adenosine A2 receptor system comprising administering a compound of formula 1to a person in need of such treatment.
Photochemical N-demethylation of alkaloids
Ripper, Justin A.,Tiekink, Edward R.T.,Scammells, Peter J.
, p. 443 - 445 (2007/10/03)
Certain alkaloids were observed to undergo N-demethylation processes under photochemical conditions. Tropine, acetyltropine, tropinone, and atropine were cleanly N-demethylated upon treatment with tetraphenylporphin, oxygen, and light. Dextromethorphan also underwent a N-demethylation reaction, but reacted further to afford an imine. In contrast, 14-acyloxycodeinones underwent a photochemically induced tandem N-demethylation-acyl migration.
ELECTRON-TRANSFER ACTIVATION. SALT EFFECTS ON THE PHOTOOXADIDATION OF TERTIARY AMINES : A USEFUL N-DEMETHYLATION METHOD
Santamaria, J.,Ouchabane, R.,Rigaudy, J.
, p. 3977 - 3980 (2007/10/02)
Photooxidation of tertiary methylamines sensitized by electron acceptors like 9,10-dicyanoanthracene is shown to proceed by two distinct ways depending on the presence of added salts.In the absence of added salt both nor and N-formyl compounds were obtained while with added salt the nor-derivative is obtained highly efficiently.
