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1.
Peter G?rtner Martin Letschnig Max Knollmüller 《Monatshefte für Chemie / Chemical Monthly》2000,3(2):867-877
Eight O-substituted 1,2-diols and one O,N-substituted 1,2-aminoalcohol derived from 2-alkoxyoctahydro-7,8,8-trimethyl-4,7-methanobenzofurans
via a [1,2]-Witting rearrangement and subsequent substitution were synthesized and tested as additives for the enantioselective addition of butyllithium
and butylmagnesium chloride to benzaldehyde and for the reduction of acetophenone with lithium aluminum hydride. The selectivity
of the reactions was determined by GC of the obtained 1-phenyl-1-pentanol and 1-phenylethanol on a chiral phase. Best results
with regard to selectivity (52% ee and 94% ee, resp.) were achieved in the formation of 1-phenyl-1-pentanol by addition of the substituted 1,2-aminoalcohol to the organometallic
reagent and in the reduction of acetophenone using an α-alkoxyalcohol (62%ee). 相似文献
2.
Dienolates of various γ-allyloxy substituted methyl β-pyrrolidinyl (E)-2-butenoate undergo a [2,3]-Wittig rearrangement to generate various 5-alkenyl-4-pyrrolidin-1-yl-5H-furan-2-one type compounds. 相似文献
3.
Manuela Weber Herbert Bartsch Thomas Erker 《Monatshefte für Chemie / Chemical Monthly》2002,133(5):653-659
Summary. Starting from 2-chloro-3-nitropyridine, 2-isopropyl-1,4-dihydropyrido[2,3-b]pyrazin-2(3H),3-dione was synthesized. This compound was reacted with potassium tert-butoxide and diethyl chlorophosphate to afford an intermediate dihydropyrido[2,3-b]pyrazin-2-ylphosphate derivative which in turn furnished the desired 1,2,4-oxadiazolylimidazo[1,5-a]pyrido[2,3-e]pyrazine derivatives with 5-alkyl-3-isocyanomethyl-1,2,4-oxadiazoles in the presence of additional tert-butoxide. The title compounds are potential ligands for the γ-aminobutyric acid A/benzodiazepine receptor complex.
Received November 26, 2001. Accepted December 3, 2001 相似文献
4.
Winfried Wendelin Edith Gößnitzer Dalal Abou El Ella 《Monatshefte für Chemie / Chemical Monthly》2000,131(4):353-374
Summary. The cyclization reactions of trans-3a-hexahydro-2-benzimidazolamine with 2-alkylidene- and 2-benzylidenecyclohexanones and α-tetralones, respectively, yield
mixtures of two isomeric condensates each. Thorough high resolution NMR analyses (1H and 13C NMR, HH-COSY, gs-HSQC, gs-HMBC, 1D TOCSY, and 1D NOE difference spectra) revealed that the corresponding isomers are in all cases linearly fused diastereomeric
12α- and 12β-substituted trans-6aα-dodecahydrobenzimidazo[2,1-b]quinazolines and 7α-substituted trans-8aβ- and trans-8aα-decahydrobenzimidazo[2,1-b]benzo[h]quinazolines, respectively. The formation of corresponding angularly fused regioisomers was not observed so far. The stereochemistry
and the tautomerism of some bases and their hydrochlorides as well as the regiospecific course of the cyclization reactions
are discussed. Biological tests showed that the novel compounds don’t exert remarkable antibacterial and antimycotic effects.
Received November 3, 1999. Accepted November 30, 1999 相似文献
5.
Michaela Wilhelm Eva Berssen Rainer Koch Henry Strasdeit 《Monatshefte für Chemie / Chemical Monthly》2002,133(8):1097-1108
Summary. Lipoyl imidazolide reacts with aza-15-crown-5 (1,4,7,10-tetraoxa-13-azacyclopentadecane) or aza-18-crown-6 (1,4,7,10,13-pentaoxa-16-azacyclooctadecane)
to afford new N-lipoylated azacrown compounds in good yields. These compounds can be transformed into 1,3-dithiols and amines by reduction
with complex hydrides of the disulfide and/or amide group of the lipoyl chain. The new pendant-arm macrocycles react as heteroditopic
ligands by forming dithiolate and disulfide complexes with the ‘soft’ metal ions Ni2+ and Pd2+, respectively, and an amine complex with the ‘hard’ Li+ ion. Semiempirical and DFT calculations on the complexation of a lithium ion give a most favourable structure in which the
azacrown and two solvent molecules are in contact with the metal but not the pendant arm.
Received January 29, 2002; accepted (revised) March 25, 2002 相似文献
6.
Summary. A series of novel tridentate ligands with nitrogen and oxygen donor sites was synthesized starting from enantiomerically
pure (S)- and (R)-1-(pyridin-2-yl)ethylamine, the preparation and resolution of which was developed. The new optically active ligands were
tested as in situ catalysts together with Ru(PPh3)3Cl2 in the enantioselective transfer hydrogenation of acetophenone with isopropanol. The secondary amine ligand (S)-2,4-di-tert-butyl-6-(1-(pyridin-2-yl)ethylamino)methylphenol gave the best results with almost quantitative conversion and 47%ee.
Received August 17, 2001. Accepted August 27, 2001 相似文献
7.
Samvel N. Sirakanyan Domenico Spinelli Athina Geronikaki Victor Kartsev Elmira K. Hakobyan Anthi Petrou Ruzanna G. Paronikyan Ivetta M. Nazaryan Hasmik H. Akopyan Anush A. Hovakimyan 《Molecules (Basel, Switzerland)》2021,26(11)
Background: Neurotic disturbances, anxiety, neurosis-like disorders, and stress situations are widespread. Benzodiazepine tranquillizers have been found to be among the most effective antianxiety drugs. The pharmacological action of benzodiazepines is due to their interaction with the supra-molecular membrane GABA-a-benzodiazepine receptor complex, linked to the Cl-ionophore. Benzodiazepines enhance GABA-ergic transmission and this has led to a study of the role of GABA in anxiety. The search for anxiolytics and anticonvulsive agents has involved glutamate-ergic, 5HT-ergic substances and neuropeptides. However, each of these well-known anxiolytics, anticonvulsants and cognition enhancers (nootropics) has repeatedly been reported to have many adverse side effects, therefore there is an urgent need to search for new drugs able to restore damaged cognitive functions without causing significant adverse reactions. Objective: Considering the relevance of epilepsy diffusion in the world, we have addressed our attention to the discovery of new drugs in this field Thus our aim is the synthesis and study of new compounds with antiepileptic (anticonvulsant) and not only, activity. Methods: For the synthesis of compounds classical organic methods were used and developed. For the evaluation of biological activity some anticonvulsant and psychotropic methods were used. Results: As a result of multistep reactions 26 new, five-membered heterocyclic systems were obtained. PASS prediction of anticonvulsant activity was performed for the whole set of the designed molecules and probability to be active Pa values were ranging from 0.275 to 0.43. The studied compounds exhibit protection against pentylenetetrazole (PTZ) seizures, anti-thiosemicarbazides effect as well as some psychotropic effect. The biological assays evidenced that some of the studied compounds showed a high anticonvulsant activity by antagonism with pentylenetetrazole. The toxicity of compounds is low and they do not induce muscle relaxation in the studied doses. According to the study of psychotropic activity it was found that the selected compounds have an activating behavior and anxiolytic effects on the models of “open field” and “elevated plus maze” (EPM). The data obtained indicate the anxiolytic (anti-anxiety) activity of the derivatives of pyrimidines, especially pronounced in compounds 6n, 6b, and 7c. The studied compounds increase the latent time of first immobilization on the model of “forced swimming” (FST) and exhibit some antidepressant effect similarly to diazepam. Docking studies revealed that compound 6k bound tightly in the active site of GABAA receptor with a value of the scoring function that estimates free energy of binding (ΔG) at −7.95 kcal/mol, while compound 6n showed the best docking score and seems to be dual inhibitor of SERT transporter as well as 5-HT1A receptor. Conclusions: Тhe selected compounds have an anticonvulsant, activating behavior and anxiolytic effects, at the same time exhibit some antidepressant effect. 相似文献
8.
A series of new optically active [2-(1-hydroxyalkyl)pyrrolidino]methylferrocenes were conveniently prepared from commercially available L-proline and ferrocenecarboxylic acid. The crystal structure of key intermediate was obtained. They were then applied to catalyze enantioselective addition of diethylzinc to arylaldehydes with enantioselectivity up to 99%. The effects of the ligand structures on the enantioselectivity were also studied. 相似文献
9.
The mass spectrometric behaviour of four cis- and trans-la, 3-disubstituted -1,1 -dichloro-4-formyl-1a,2,3,4-tetrahydro-1H-azirino[1, 2-a] [1,5] benzodiazepines has been studied with the aid of mass-analysed ion kinetic energy spectrometry and exact mass measurements under electron impact ioniza-tion. All compounds show a tendency to eliminate a chlorine atom from the aziridine ring, and then eliminate a neutral propene or styrene from the diazepine ring to yield azirino[ 1, 2-6][1,3]benzimidazole ions. These azmno[1,2-a] [1,5]-benzodiazepines can also eliminate HCl, or Cl plus HG simultaneously to undergo a ring enlargement rearrangement to yield 1,6-benzodiazocine ions, which further lose small molecular fragments, propyne or phenylacetylene, with rearrangement to give quinoxaline ions. 相似文献
10.
Osama I. Abd El-Salam 《Monatshefte für Chemie / Chemical Monthly》2000,131(9):959-965
Summary. The synthesis of new pyrimido[5,4-a]indolizines by reaction of 2-aminoindolizine-1-carbonitrile or ethyl 2-aminoindolizine-1-carboxylate with various electrophilic
reagents is described. The structure of the products was confirmed by their elemental analysis and IR, 1H NMR, and mass spectra. The results of a preliminary antimicrobial screening are also presented.
Received February 4, 2000. Accepted (revised) March 8, 2000 相似文献
11.
环己酮与硫代碳酰肼在不同介质中的反应,合成出两个不同的环己烷螺含氮杂环化合物。经X-射线结构分析确定它们分别为1,2,4,5-四氮螺[5,5]十一烷-3-硫酮,C_7H_(14)N_4S(Ⅰ)和1,2,4,-三氮螺[4,5]癸-1-烯-4-氨基-3-硫酮。C_7H_(12)N_4S_x(S_x=0.8S+0.2O)(Ⅱ)。晶体学参数分别为(Ⅰ):P2_1/c,a=12.026(4),b=26.817(6),c=12.042(3),β=115.94(2)°,Z=4,V=933.4(10),M_r=186.28;(Ⅱ):P2_1/m,a=6.595(7),b=6.817(6),c=10.572(6),β=106.3(1)°,V=456(1),Z=2,M_r=181.05。最终一致因子分别为R=0.054,R_w=0.065和R=0.089,R_w=0.096。两个化合物中,环己烷都为椅式构型,它与其螺联的6员氮杂环,5员氮杂环的最小二乘平面间的夹角分别为68.94和90°。并对合成反应途径作了初步讨论。 相似文献
12.
Summary. GABA-receptor-ligands are still very interesting in drug-development. Usually benzodiazepines are used in the treatment but they
have serious side-effects. Thus, a recently synthesized quioxaline derivative which showed reduced side-effects in an animal
model was used as a model-substance. The cyclus was modified to optimize the pharmacological profile. Accordingly, a series
of imidazo-thieno-thiazines was synthesized starting from 5-acetyl-2-chloro-3-nitrothiophene to yield 6-ethyl-2,3-dihydro-1H-thieno[2,3-b][1,4]thiazine-2-one. Reaction with potassium tert-butoxide and diethylchlorophosphate gave an intermediate, which resulted in the desired ring system after adding the corresponding
isocyanides and potassium tert-butoxide.
Corresponding author. E-mail: thomas.erker@univie.ac.at
Received August 6, 2002; accepted August 13, 2002 相似文献
13.
14.
Jun Min HUANG* Ru Yu CHEN Institute of Elemento-Organic Chemistry Nankai University Tianjin 《中国化学快报》2001,(12)
During the past two decades, a-ketophosphonates and their derivatives have attracted considerable attention because of their special physical, chemical and pharmacological properties due to the proximity of the carbonyl and the phosphoryl groups1-12. In the study on new pharmaceuticals and agrochemicals, the application of heterocycles is suggested to improve the biological activity. A sizeable number of endogenous fused heterocyclic compounds play a key role in regulation of various life pr… 相似文献
15.
Summary. Starting from 2-chloro-3-nitropyridine, 1H-pyrido[2,3-b][1,4]thiazin-2(3H)-one was synthesized. This compound was reacted with potassium tert-butoxide and diethyl chlorophosphate to give the intermediate 1H-pyrido[2,3-b][1,4]thiazin-2-ylphosphate derivative, which in turn afforded the 1,2,4-oxadiazolylimidazo[1,5-d]pyrido[2,3-b]pyrazine derivatives. The title compounds are potential ligands for the γ-aminobutyric acid A/benzodiazepine receptor complex.
Corresponding author. E-mail: thomas.erker@univie.ac.at
Received February 22, 2002. Accepted March 6, 2002 相似文献
16.
17.
The title compound 7-ethoxycarbonyl-2-methyl-6-methylthio-lH-imidazo[1,2-b]- pyrazole (Mr = 239.29) was synthesized and structurally characterized by IR, ^1H NMR and single-crystal X-ray diffraction. It belongs to the triclinic system, space group P1, with a =8.0461(10), b = 8.5534(11), c = 9.5605(12)А,α= 64.804(2),β= 74.231(2), γ= 76.885(2)°, V = 568.27(12)А^3, Z = 2,Dc= 1.398 g/cm^3,μ= 0.274 nunl, F(000) - 252, the final R = 0.0454 and wR = 0.1261. A total of 3360 reflections were collected, of which 2466 were independent (R_int = 0.0138) and 2154 were observed with I〉2σ(I). 相似文献
18.
取代苯乙烯基吡啶并[1,2—a]吲哚盐的合成及^1H NMR研究 总被引:1,自引:0,他引:1
8,10,10-三甲基-10H-吡啶并[1,2-a]吲哚高氯酸盐与取代苯甲醛在六氢吡啶催化下缩合得到12种新的8-取代苯乙烯基-10,10-二甲基-10H吡啶并[1,2-a]吲哚高氯酸盐,经元素分析和波谱确定其结构。讨论了取代基对各类质子化学位移的影响,找出了δ与取代基常数间定量关系。 相似文献
19.
20.
Shi Liang HUANG Yi LUO Zhi Shu HUANG Xian Zhang BU Pei Qing LIU Lin MA Yue Ming LI Albert S. C. CHAN Lian Quan GU 《中国化学快报》2006,17(6):769-772
Mansonone compounds represent a series of naturally occurring o-quinones mainly isolated from the heartwood of Mansonia Altissima1 and Ulmus Glabra2. Mansonone F contained oxaphenalene skeleton which was a relatively novel structure and rarely existed in … 相似文献