Synthesis of the Cyclic Isomer of the Vitamin K1 Dihydro Derivative (Naphthotocopherol) and Its Analogues with the Shortened, and ω-Functionalized Side Chain.

ChemInform ◽  
2006 ◽  
Vol 37 (18) ◽  
Author(s):  
A. Yu. Spivak ◽  
O. V. Knyshenko ◽  
M. I. Mallyabaeva ◽  
V. N. Odinokov
1984 ◽  
Vol 51 (03) ◽  
pp. 358-361 ◽  
Author(s):  
H Bechtold ◽  
K Andrassy ◽  
E Jähnchen ◽  
J Koderisch ◽  
H Koderisch ◽  
...  

SummaryIn 8 patients on no oral intake and with parenteral alimentation, administration of cephalosporins with N-methyl-thiotetrazole side chain (moxalactam, cefamandole), was associated with prolongation of prothrombin time, appearance in the circulation of descarboxy-prothrombin (counter immunoelectrophoresis and echis carinatus assay) and diminution of protein C. Acute administration of 10 mg vitamin Ki was followed by the transient appearance of vitamin K1 2,3-epoxide, indicating an impaired hepatocellular regeneration of vitamin K1 from the epoxide. Impaired hepatic vitamin K1 metabolism, tentatively ascribed to the N-methyl-thiotetrazole group, is one (but possibly not the only) cause of bleeding complications and depression of vitamin K1dependent procoagulants in patients treated with the new class of cephalosporins.


1967 ◽  
Vol 45 (7) ◽  
pp. 751-757 ◽  
Author(s):  
Stewart McLean ◽  
A. G. Harrison ◽  
D. G. Murray

11-Oxotetrahydrorhombifoline (I) has been isolated from the alkaloidal extract of the bark of Ormosia coutinhoi, and its dihydro derivative II has been prepared. An examination of the mass spectra of these compounds and of their 3,3-d2 derivatives has led to the elucidation of the course of the major electron impact induced fragmentations undergone by the molecules. The main fragmentation of I leads to loss of C3H5 from the side chain to form an ion of m/e 221, with a minor path involving a central fission of the molecular ion to form an ion of m/e 150. The mass spectrum of II shows that the loss of C3H7 to form the ion of m/e 221 is a minor process, the main fragmentation reaction involving a central fission to form an ion of m/e 152 analogous to the ion of m/e 150 from I. This change in the spectrum is shown to be consistent with predictions based on the quasi-equilibrium theory of mass spectra.


ChemInform ◽  
2010 ◽  
Vol 33 (34) ◽  
pp. no-no
Author(s):  
V. N. Odinokov ◽  
A. Yu. Spivak ◽  
G. A. Emelianova ◽  
B. I. Kutepov ◽  
L. M. Khalilov

1989 ◽  
Vol 54 (1) ◽  
pp. 235-247 ◽  
Author(s):  
Zdeněk Polívka ◽  
Vladimír Valenta ◽  
Karel Šindelář ◽  
Jiří Holubek ◽  
Miloš Buděšínský ◽  
...  

Reduction of IV with hydroiodic acid afforded almost quantitatively the spirocyclic amino sulfide VII, evidently via V and VI. The carbamate II was chlorinated with N-chlorosuccinimide, the product (XII) was reacted with phenylmagnesium bromide and then reduced with LiAlH4 to give the 6-phenyl derivative X of the antidepressant agent hydrothiadene (I). Treatment of 11-methyl-6,11-dihydrodibenzo[b,e]thiepin (XIII) with butyllithium followed by alkylation with 3-dimethylaminopropyl chloride resulted in 6-(3-dimethylaminopropyl) derivative XIV. Reaction of XIV with ethyl chloroformate and the following alkaline hydrolysis gave the 6-(3-methylaminopropyl) derivative XV (mixture of stereoisomers). Reduction of the corresponding olefinic amine and the tertiary alcohol with hydroiodic acid gave the saturated side chain amines derived from 4,9-dihydrothieno[2,3-c]-2-benzothiepin XVIII and XIX. The dihydro derivative of dithiadene XVIII (VÚFB-17 031) proved very effective in a series of tests predictive of antidepressant activity.


1993 ◽  
Vol 26 (21) ◽  
pp. 5657-5663 ◽  
Author(s):  
Satya B. Sastri ◽  
Samuel I. Stupp

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