41103-43-9Relevant academic research and scientific papers
Manganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis
Das, Kuhali,Sarkar, Koushik,Maji, Biplab
, p. 7060 - 7069 (2021/06/30)
Controlling the selectivity in a hydroamination reaction is an extremely challenging yet highly desirable task for the diversification of amines. In this article, a selective formal anti-Markovnikov hydroamination of allyl alcohols is presented. It enables the versatile synthesis of valuable γ-amino alcohol building blocks. A phosphine-free Earth's abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of aliphatic, aromatic amines, drug molecules, and natural product derivatives underwent successful hydroamination with primary and secondary allylic alcohols with excellent functional group tolerance (57 examples). The catalysis could be performed on a gram scale and has been applied for the synthesis of drug molecules. The mechanistic studies revealed the metal-ligand bifunctionality as well as hemilability of the ligand backbone as the key design principle for the success of this catalysis.
Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols
Ma, Wei,Zhang, Xiaohui,Fan, Juan,Liu, Yuxuan,Tang, Weijun,Xue, Dong,Li, Chaoqun,Xiao, Jianliang,Wang, Chao
supporting information, p. 13506 - 13515 (2019/09/09)
Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.
New 99mTc(CO)3-radiolabeled arylpiperazine pharmacophore as potent 5HT1A serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling, and biological evaluation
Erfani, Mostafa,Malek, Hadi,Sadat Ebrahimi, Seyed Esmaeil,Hassanzadeh, Leila
, p. 166 - 177 (2019/03/21)
In spite of previous efforts, there is lack of a radiotracer for imaging the 5HT1A receptor density in human brain, which is involved in several neurological brain disorders. The aim of this study was to prepare a new derivative of 1-(2-methoxyphenyl)piperazine (MPP) as a main chemical structure of 5HT1A receptor antagonist with 3-carbon linker and radiolabeled by [99mTc][Tc(CO)3(H2O)3]+ precursor. Docking studies before chemical synthesis showed similar fashion of interaction for both WAY100635 (potent 5HT1A receptor antagonist) and new designed ligand, despite of addition of 99mTc(CO)3 group in the structure of new ligand. MPP-(CH2)3-N3 was synthesized via three efficient and reliable chemical synthesis steps (more than 80% yield) then radiolabeled by addition of 2-ethynylpyridine and [99mTc][Tc(CO)3(H2O)3]+ precursor in one pot procedure (more than 95% radiochemical efficiency) through click chemistry method. After incubation, radiotracer was found stable in vitro up to 2?hours. Binding assays showed about 33% specific binding of radiotracer to the 5HT1A receptors. Brain biodistribution studies indicated (0.26?±?0.05)% ID/g hippocampus uptake at 30?minutes post injection, which its specificity was verified through blocking studies. These results suggested that new designed radioligand might serve as a potent SPECT imaging agent to estimate status of 5HT1A receptors.
2-Amino-3-(1-(4-(4-(2-methoxyphenyl) piperazine-1-yl)butyl)-1H-1,2,3- triazol-4-yl) propanoic acid: Synthesized, 99mTc-tricarbonyl labeled, and bioevaluated as a potential 5HT1A receptor ligand
Hassanzadeh, Leila,Sadat Ebrahimi, Seyed Esmaeil,Erfani, Mostafa
, p. 371 - 376,6 (2020/08/24)
To develop a novel 5HT1A receptor imaging agent, a new methoxyphenyl piperazine derivative was synthesized and radiolabeled with 99mTc-tricarbonyl precursor. We used the Cu (I)-catalyzed cycloaddition of azide and terminal alkynes to
MEDICAMENTS
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Page/Page column 92, (2009/06/27)
A compound of formula (I) is described: wherein R1 and R2 are as defined in the text and wherein the compounds are intended for use in treating medical conditions characterized by an imbalance in dopamine receptor activity.
N-[3-[4-(2-methoxyphenyl) piperaziny-1-yl]propyl]cyclam: Synthesized as a potential 5-HT1A receptor ligand and labelled with 99mTc-nitrido core
Wang, Fenglong,Wang, Xuebin,Yang, Shuye,Liu, Jian,Zhang, Xianzhong
experimental part, p. 347 - 351 (2009/04/07)
This paper reports the synthesis of new potential 5-HT1A receptor ligand N-[3-[4-(2-methoxyphenyl)piperaziny-1-yl]propyl]cyclam (MPPC) and radiolabelling of it with 99mTc-nitrido core. The novel neutral complex 99mTcN-MPPC
COMPSITIONS, SYNTHESIS, AND METHODS OF USING QUINOLINE BASED ATYPICAL ANTIPSYCHOTIC AGENTS
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Page/Page column 27-28, (2009/01/20)
The present invention provides novel quinolinone derivatives which can be advantageously used for treating schizophrenia and related psychoses such as acute manic, bipolar disorder, autistic disorder, and depression.
Utility of azetidinium methanesulfonates for radiosynthesis of 3-[ 18F]fluoropropyl amines
Kiesewetter, Dale O.,Eckelman, William C.
, p. 953 - 969 (2007/10/03)
3-Methanesulfonyloxypropyl tertiary amines were observed to cyclize to form azetidinium methanesulfonate moieties. Heat-induced cyclization of 3-methanesulfonyloxypropyl amines was utilized for preparation of azetidinium methanesulfonates. The azetidinium methanesulfonates were found to incorporate radioactive [18F]fluoride (decay-corrected yields > 60%) efficiently, resulting in an efficient synthesis of 3-[18F] fluoropropyl tertiary amines. Copyright
N-Arylpiperazinyl-N'-propylamino derivatives of heteroaryl amides as functional uroselective α1-adrenoceptor antagonists
Elworthy, Todd R.,Ford, Anthony P. D. W.,Bantle, Gary W.,Morgans Jr., David J.,Ozer, Rachel S.,Palmer, Wylie S.,Repke, David B.,Romero, Magarita,Sandoval, Leticia,Sjogren, Eric B.,Talamás, Francisco X.,Vazquez, Alfredo,Wu, Helen,Arredondo, Nicolas F.,Blue Jr., David R.,DeSousa, Andrea,Gross, Lisa M.,Kava, M. Shannon,Lesnick, John D.,Vimont, Rachel L.,Williams, Timothy J.,Zhu, Quan-Ming,Pfister, Jürg R.,Clarke, David E.
, p. 2674 - 2687 (2007/10/03)
Novel arylpiperazines were identified as α1-adrenoceptor (AR) subtype- selective antagonists by functional in vitro screening. 3-[4-(ortho- Substituted phenyl)piperazin-1:yl]propylamines were derivatized with N,N- dimethyl anthranilamides, nicotinamides, as well as carboxamides of quinoline, 1,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4- b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta were used as a 'negative screen' for the test antagonists. Binding to α1-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g. 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the α1-AR subtype prevalent in the human lower urinary tract (pA2 values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the α(1D)-AR.
Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moities
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, (2008/06/13)
A series of 1,4-dihydropyridin-3,5-yl dicarboxylic acid amides and esters incorporating an arylpiperazinylalkyl moiety have been prepared possessing the general formula STR1 wherein R4 is cycloalkyl, aryl or hetaryl, generally with electronwithdrawing substituents; R2 and R6 are lower alkyl, alkanol, alkoxyalkyl, or alkylaminoalkyl; R5 is R2 or arylpiperazinylalkyl; X is 0 or NH; Y is lower alkylene, alkoxyalkylene, alkylaminoalkylene; and Z is phenyl, substituted phenyl, pyridinyl, substituted pyridinyl, or pyrimidinyl. Compounds of this series demonstrate activity as calcium and alphaadrenergic blockers in in vitro testing and antihypertensive, antiischemic, and platelet function inhibiting actions in in vivo screens.
