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1.
Robert Weis Marcel Kaiser Reto Brun Robert Saf Werner Seebacher 《Monatshefte für Chemie / Chemical Monthly》2006,31(6):1365-1374
4-Aminobicyclo[2.2.2]octan-2-ones and -ols showed activity against the causative organisms of East African sleeping sickness
and Malaria tropica. Several imino derivatives of the ketones were more active. Now hydrazono analogues and 3-hydroximino
derivatives of the ketones and alcohols were synthesized. The structures of the obtained isomers were elucidated by NMR spectroscopy.
A single phenylhydrazone exhibited quite good antitrypanosomal activity in the range of already known imino analogues. 相似文献
2.
Robert Weis Reto Brun Robert Saf Werner Seebacher 《Monatshefte für Chemie / Chemical Monthly》2003,134(7):1019-1026
Summary. 4-Aminobicyclo[2.2.2]octanones which were prepared in one-pot-reactions from benzylidene acetone and dialkylammonium rhodanides
were reduced stereoselectively to their corresponding alcohols. The activities of the bicyclic compounds against causative
organisms of tropical deseases were examined. The 4-aminobicyclo[2.2.2]octan-2-ols were in general more active against Trypanosoma b. rhodesiense and Plasmodium falciparum than the corresponding keto compounds.
Corresponding author. E-mail: robert.weis@uni-graz.at
Received November 27, 2002; accepted December 2, 2002
Published online May 2, 2003 相似文献
3.
Robert Weis Reto Brun Robert Saf Werner Seebacher 《Monatshefte für Chemie / Chemical Monthly》2003,42(6):1019-1026
4-Aminobicyclo[2.2.2]octanones which were prepared in one-pot-reactions from benzylidene acetone and dialkylammonium rhodanides
were reduced stereoselectively to their corresponding alcohols. The activities of the bicyclic compounds against causative
organisms of tropical deseases were examined. The 4-aminobicyclo[2.2.2]octan-2-ols were in general more active against Trypanosoma b. rhodesiense and Plasmodium falciparum than the corresponding keto compounds. 相似文献
4.
Werner Seebacher Heinrich Berger Marcel Kaiser Reto Brun Robert Saf Robert Weis 《Monatshefte für Chemie / Chemical Monthly》2006,137(4):471-482
Summary. Several 4-aminobicyclo[2.2.2]octan-2-ones and -ols were synthesized using different pathways. The new compounds were investigated
for their activity against Trypanosoma b. rhodesiense, the causative organism of East African sleeping sickness and Plasmodium falciparum the protozoan parasite which causes Malaria tropica. The results are compared to the activities of known compounds and the
influence of the substitution of the bicyclo[2.2.2]octane skeleton on the biological activities is discussed. 相似文献
5.
Summary. 4-Aminobicyclo[2.2.2]octanones were converted to their N-oxides and to 4-aminobicyclo[2.2.2]octanes. Furthermore, the 6,7-bis-(4-methoxyphenyl) analogues were synthesized. All products were screened for their activities against Trypanosoma b. rhodesiense and Plasmodium falciparum. The pharmacological results were compared with those of formerly tested bicyclo[2.2.2]octanones and bicyclo[2.2.2]octanols. Structure-activity relationships are discussed.Received April 8, 2003; accepted April 14, 2003
Published online September 25, 2003 相似文献
6.
Summary. New derivatives of 4-aminobicyclo[2.2.2]octanones and -ols were prepared. Their structures were established by means of NMR experiments. All new compounds were tested for their activities against Plasmodium falciparum and Trypanosoma b. rhodesiense. One of the bicyclooctanols showed promising antitrypanosomal activity. 相似文献
7.
Werner Seebacher Reto Brun Robert Saf Dietmar Kr?pfl Robert Weis 《Monatshefte für Chemie / Chemical Monthly》2004,31(6):313-322
New derivatives of 4-aminobicyclo[2.2.2]octanones and -ols were prepared. Their structures were established by means of NMR experiments. All new compounds were tested for their activities against Plasmodium falciparum and Trypanosoma b. rhodesiense. One of the bicyclooctanols showed promising antitrypanosomal activity. 相似文献
8.
Werner Seebacher Heinrich Berger Marcel Kaiser Reto Brun Robert Saf Robert Weis 《Monatshefte für Chemie / Chemical Monthly》2006,31(6):471-482
Several 4-aminobicyclo[2.2.2]octan-2-ones and -ols were synthesized using different pathways. The new compounds were investigated
for their activity against Trypanosoma b. rhodesiense, the causative organism of East African sleeping sickness and Plasmodium falciparum the protozoan parasite which causes Malaria tropica. The results are compared to the activities of known compounds and the
influence of the substitution of the bicyclo[2.2.2]octane skeleton on the biological activities is discussed. 相似文献
9.
Werner Seebacher Reto Brun Robert Saf Robert Weis 《Monatshefte für Chemie / Chemical Monthly》2003,17(9):1411-1420
4-Aminobicyclo[2.2.2]octanones were converted to their N-oxides and to 4-aminobicyclo[2.2.2]octanes. Furthermore, the 6,7-bis-(4-methoxyphenyl) analogues were synthesized. All products were screened for their activities against Trypanosoma b. rhodesiense and Plasmodium falciparum. The pharmacological results were compared with those of formerly tested bicyclo[2.2.2]octanones and bicyclo[2.2.2]octanols. Structure-activity relationships are discussed. 相似文献
10.
Robert Weis Marcel Kaiser Reto Brun Robert Saf Werner Seebacher 《Monatshefte für Chemie / Chemical Monthly》2008,31(6):717-724
5-Amino-2-azabicyclo[3.2.2]nonanes possess activity against the causative organisms of Human African trypanosomiasis and Malaria tropica. Their newly prepared N-acyl derivatives were inactive against Trypanosoma b. rhodesiense, but some of them showed good antiplasmodial activity against a multiresistant strain of Plasmodium falciparum. The results are compared to the activities of the N-unsubstituted compounds and N-sulfonyl analogues. The diastereomeric character of the formed amides was elucidated by NMR spectroscopy. 相似文献
11.
Lucjusz Zaprutko Dorota Olender Andrzej Gzella 《Monatshefte für Chemie / Chemical Monthly》2003,134(8):1145-1150
Summary. Reactions of 1-phenacyl derivatives of 2-methyl-4,5-dinitroimidazole with primary or secondary amines (aniline, morpholine, piperidine, pyrrolidine) yielded the 4-amino-5-nitroimidazole derivatives only.Received January 23, 2003; accepted (revised) February 5, 2003
Published online June 2, 2003 相似文献
12.
Werner Seebacher Marcel Kaiser Reto Brun Robert Saf Robert Weis 《Monatshefte für Chemie / Chemical Monthly》2007,138(6):619-625
Summary. Several 2-substituted 4-amino-2-azabicyclo [3.2.2]nonane derivatives were synthesized. The new compounds were investigated
for their activities against the causative organism of East African sleeping sickness, Trypanosoma b. rhodesiense, and a protozoan parasite which causes Malaria tropica, Plasmodium falciparum K1, a strain which is resistant to chloroquine and pyrimethamine. The results are compared to the activities of 2-unsubstituted
4-amino-2-azabicyclo[3.2.2]nonanes. 相似文献
13.
Summary. The synthesis of new bicyclo[2.2.2]octane derivatives is described and their structures were established by NMR experiments. All compounds were tested in in vitro assays for their activities against causative organisms of malaria and African sleeping sickness and compared to those of former synthesized compounds. 相似文献
14.
Werner Seebacher Marcel Kaiser Reto Brun Robert Saf Robert Weis 《Monatshefte für Chemie / Chemical Monthly》2005,7(5):625-634
The synthesis of new bicyclo[2.2.2]octane derivatives is described and their structures were established by NMR experiments. All compounds were tested in in vitro assays for their activities against causative organisms of malaria and African sleeping sickness and compared to those of former synthesized compounds. 相似文献
15.
16.
Werner Seebacher Marcel Kaiser Reto Brun Robert Saf Robert Weis 《Monatshefte für Chemie / Chemical Monthly》2007,138(7):709-714
Summary. We synthesized several 4-aminobicyclo[2.2.2] octan-2-ols and 4-amino-2-azabicyclo[3.2.2]nonanes from epimerized 4-amino-bicyclo[2.2.2]octan-2-ones.
The new compounds were tested for their activity against Trypanosoma b. rhodesiense, the causative organism of East African sleeping sickness, and Plasmodium falciparum K
1, a multiresistant protozoan parasite which causes Malaria tropica. The results are compared to the activities of their formerly
synthesized stereoisomers and structure–activity relationships are discussed. 相似文献
17.
The 13C n.m.r. data of a variety of 4eq- and 4ax-substituted adamantanones and bicyclo[2.2.2]octanones are presented. It is shown that for a number of carbons the chemical shifts cannot be predicted by a given additivity rule. The deviations of the observed chemical shifts from the calculated ones are discussed in terms of different interaction mechanisms operating through the σ bond frameworks or through space. 相似文献
18.
Mayya Korochkina Alessandro Casnati Arturo Arduini Rocco Ungaro Vladimir Kataev Vladimir Alfonsov 《Tetrahedron》2005,61(23):5457-5463
Novel calix[4]arene derivatives functionalized with two or four isosteviol units at the upper rim and a new calix[6]arene having six isosteviol moieties at the lower rim have been synthesized. The structures of these compounds have been confirmed by NMR and mass spectrometry data. All 1H and 13C NMR chemical shifts of isosteviol were fully assigned by extensive NMR spectroscopic methods, and used to clarify the structures and conformations of isosteviol-calixarene conjugates. 相似文献
19.
20.
Structure and Properties of the Hydridomethyltetrafluorophosphate Anion, [CH3PF4H]— Methyltrifluorphosphorane reacts with strong fluoride donors like CsF, (CH3)4NF and (CH3)4PF with formation of the corresponding hydridomethyltetrafluorophosphates. The salts are characterized by NMR, IR and Raman spectroscopy. The experimental results show that only the trans isomer is formed. For both isomers theoretical calculations (B3LYP/6‐31+G* and RHF/6‐31+G*) were carried out. The difference for the Gibbs free energy between the isomers was calculated to be 35.4 kJ/mol (B3LYP/6‐31+G*). The RHF/6‐31+G* calculation yields, for the almost octahedral trans isomer, bond distances of r(PF) = 167 pm, r(PC) = 184.5 pm and r(PH) = 138.1 pm. 相似文献