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Eco-friendly synthesis of ionic helical polymers and their chemical properties and reactivity
Reaction of N-(2,4-dinitrophenyl)pyridinium chloride (salt(Cl-)) with sodium dicyanamide (Na(CN)2N) resulted in anion exchange between Cl- and (CN)2N- to yield a new Zincke salt, salt((CN)2N-). Reactions of salt((CN)2N-) with piperazine, specifically (R)-(-)- or (S)-(+)-2-methylpiperazine under eco-friendly conditions, such as in aqueous solution, in the absence of a catalyst, and at room temperature, resulted in pyridinium ring opening to yield ionic high-molecular-weight polymers with 5-2,4-dienylideneammonium dicyanamide units or chiral 5-(2-methylpiperazinium)-2,4-dienylideneammonium dicyanamide units, namely, polymer(H;(CN)2N-), polymer(R-Me;(CN)2N-), and polymer(S-Me;(CN)2N-). UV-Vis measurements revealed that the π-conjugation system expanded along the polymer chain due to the orbital interaction between the electrons on the two nitrogen atoms of the piperazinium ring. Circular dichroism (CD) measurements revealed a helical conformation of the main chain in polymer(R-Me;(CN)2N-) and polymer(S-Me;(CN)2N-). The reaction of polymer(H;(CN)2N-) with p-phenylenediamine (PDA) caused recyclization of the 2,4-dienylideneammonium unit and resulted in depolymerization to yield N-(4-aminophenyl)pyridinium dicyanamide. Cyclic voltammetry analysis suggested that the polymers obtained in this study undergo electrochemical oxidation and reduction.
Yamaguchi, Isao,Tanaka, Yuki,Wang, Aohan
p. 29988 - 29994
(2018)
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Method for protecting sulfonyl of deamination amine
The invention discloses a method for removing sulfenyl protection of amine. The method comprises the following steps: dissolving N - sulfonyl-protected amine and a base in a reaction solvent, then adding diphenylphosphine to uniformly mix and maintain 90 °C. When TCL detection reaction is complete, a recrystallization method or an extraction separation method is adopted to obtain the target product. The method disclosed by the invention adopts diphenylphosphine as an extraction reagent, is good in reaction activity, high in selectivity and wide in application range, and can replace the use of a hazardous reagent under the basic heating condition. Prodrug research and development and industrial production are of great significance.
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Paragraph 0027-0029

(2021/11/03)

MONOACYLGLYCEROL LIPASE INHIBITORS
Provided are compounds of formula (I), or a pharmaceutically acceptable salt or solvate thereof: Also provided are compositions comprising compounds of formula (I). The compounds and compositions are also provided for use as medicaments, for example as medicaments useful in the treatment of a condition modulated by monoacylglycerol lipase (MAGL). Also provided are the use of compounds and compositions for the inhibition of monoacylglycerol lipase (MAGL).
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Paragraph 0111-0112; 0141; 0153-0154

(2021/09/09)

Indirect reduction of CO2and recycling of polymers by manganese-catalyzed transfer hydrogenation of amides, carbamates, urea derivatives, and polyurethanes
The reduction of polar bonds, in particular carbonyl groups, is of fundamental importance in organic chemistry and biology. Herein, we report a manganese pincer complex as a versatile catalyst for the transfer hydrogenation of amides, carbamates, urea derivatives, and even polyurethanes leading to the corresponding alcohols, amines, and methanol as products. Since these compound classes can be prepared using CO2as a C1 building block the reported reaction represents an approach to the indirect reduction of CO2. Notably, these are the first examples on the reduction of carbamates and urea derivatives as well as on the C-N bond cleavage in amides by transfer hydrogenation. The general applicability of this methodology is highlighted by the successful reduction of 12 urea derivatives, 26 carbamates and 11 amides. The corresponding amines, alcohols and methanol were obtained in good to excellent yields up to 97%. Furthermore, polyurethanes were successfully converted which represents a viable strategy towards a circular economy. Based on control experiments and the observed intermediates a feasible mechanism is proposed.
Liu, Xin,Werner, Thomas
p. 10590 - 10597
(2021/08/20)

Nickel-Catalyzed Amination of Aryl Chlorides with Amides
A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.
Li, Jinpeng,Huang, Changyu,Wen, Daheng,Zheng, Qingshu,Tu, Bo,Tu, Tao
supporting information
p. 687 - 691
(2021/01/09)

Discovery and characterization of an acridine radical photoreductant
Photoinduced electron transfer (PET) is a phenomenon whereby the absorption of light by a chemical species provides an energetic driving force for an electron-transfer reaction1–4. This mechanism is relevant in many areas of chemistry, including the study of natural and artificial photosynthesis, photovoltaics and photosensitive materials. In recent years, research in the area of photoredox catalysis has enabled the use of PET for the catalytic generation of both neutral and charged organic free-radical species. These technologies have enabled previously inaccessible chemical transformations and have been widely used in both academic and industrial settings. Such reactions are often catalysed by visible-light-absorbing organic molecules or transition-metal complexes of ruthenium, iridium, chromium or copper5,6. Although various closed-shell organic molecules have been shown to behave as competent electron-transfer catalysts in photoredox reactions, there are only limited reports of PET reactions involving neutral organic radicals as excited-state donors or acceptors. This is unsurprising because the lifetimes of doublet excited states of neutral organic radicals are typically several orders of magnitude shorter than the singlet lifetimes of known transition-metal photoredox catalysts7–11. Here we document the discovery, characterization and reactivity of a neutral acridine radical with a maximum excited-state oxidation potential of ?3.36 volts versus a saturated calomel electrode, which is similarly reducing to elemental lithium, making this radical one of the most potent chemical reductants reported12. Spectroscopic, computational and chemical studies indicate that the formation of a twisted intramolecular charge-transfer species enables the population of higher-energy doublet excited states, leading to the observed potent photoreducing behaviour. We demonstrate that this catalytically generated PET catalyst facilitates several chemical reactions that typically require alkali metal reductants and can be used in other organic transformations that require dissolving metal reductants.
MacKenzie, Ian A.,Wang, Leifeng,Onuska, Nicholas P. R.,Williams, Olivia F.,Begam, Khadiza,Moran, Andrew M.,Dunietz, Barry D.,Nicewicz, David A.
p. 76 - 80
(2020/04/17)

Design, synthesis, and biological evaluation of structurally constrained hybrid analogues containing ropinirole moiety as a novel class of potent and selective dopamine D3 receptor ligands
Two series of hybrid analogues were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine D3 receptor. Binding affinities of target compounds were determined (using the method of radioligand binding assay). Compared to comparator agent BP897, compounds 2a and 2c were found to demonstrate a considerable binding affinity and selectivity for D3 receptor, and especially compound 2h was similarly potent and more selective D3R ligand than BP897, a positive reference. Thus, they may provide valuable information for the discovery and development of highly potent dopamine D3 receptor ligands with outstanding selectivity.
Zhou, Benhua,Hong, Kwon Ho,Ji, Min,Cai, Jin
p. 1597 - 1609
(2018/07/31)

New organometallic imines of rhenium(i) as potential ligands of GSK-3β: Synthesis, characterization and biological studies
Substituted amino-piperazine derivatives were synthesized and used as precursors for the preparation of a series of new organometallic Re(i) imine complexes with the general formula [(η5-C5H4CHN-(CH2)5-Pz-R)Re(CO)3] (Pz-R: -alkyl or aryl piperazine). The piperazine-based ligands were designed to be potential inhibitors of GSK-3β kinase. All the ligands and complexes were fully characterized and evaluated against the HT-29 and PT-45 cancer cell lines, in which GSK-3β plays a crucial role. In this context, we carried out biological evaluation using the MTT colorimetric assay. In terms of structure activity relationship, our findings indicated improved biological activity when aromaticity increased in the organic ligands (3d). In addition, the presence of the rhenium fragment in the imines (5a-d) leads to better activity with IC50 values in the range of 25-100 μM. In addition, our experimental studies were complemented by computational studies, where the volume and electrostatic surface of the organic ligands and organometallic compounds as well as their binding to the kinase protein are calculated.
Mu?oz-Osses, Michelle,Godoy, Fernando,Fierro, Angélica,Gómez, Alejandra,Metzler-Nolte, Nils
p. 1233 - 1242
(2018/02/07)

Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine-3-carboxamide derivatives
We report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against drug-sensitive/resistant MTB strains, and they have acceptable safety indices against MTB H37Rv with the SI values of 4395 and 1405, respectively. Moreover, N-[2-(piperazin-1-yl)ethyl] moiety was also identified as a potentially alternative linker (compound 31), opening a new direction for further SAR studies.
Lv, Kai,Li, Linhu,Wang, Bo,Liu, Mingliang,Wang, Bin,Shen, Weiyi,Guo, Huiyuan,Lu, Yu
p. 117 - 125
(2017/06/05)

Organonickel complexes encumbering bis-imidazolylidene carbene ligands: Synthesis, X-ray structure and catalytic insights on Buchwald-Hartwig amination reactions
New four coordinated homoleptic bis(diimidazolylidene)nickel(II) complexes (C1 & C2) were synthesized and characterized by elemental analysis, NMR (1H and13C) as well as ESI-Mass spectrometry. The molecular structure of the complex C1 was identified by means of single-crystal X-ray diffraction analysis, which revealed that the complexes possess a distorted square planar geometry with chelating bis(diimidazolylidene) NHC ligands and two non coordinating bromide counter ions in tetradentate C4fashion. A survey of their catalytic activity in Buchwald?Hartwig amination has been performed. The newly synthesized complexes also catalyzed the amination of aryl chlorides in the presence of KOtBu. Various aryl chlorides and amines can react smoothly to give the corresponding aminated products in moderate to high yields. The scope of the reaction encompasses electronically varied aryl chlorides and nitrogen-containing heteroaryl chlorides, including pyridine and quinoline derivatives. Both secondary and primary amines are well tolerated under the optimal reaction conditions.
Nirmala, Muthukumaran,Saranya, Gandhi,Viswanathamurthi, Periasamy,Bertani, Roberta,Sgarbossa, Paolo,Malecki, Jan Grzegorz
supporting information
p. 1 - 10
(2017/01/09)

n-Butyllithium-mediated synthesis of N-aryl tertiary amines by reactions of fluoroarenes with secondary amines at room temperature
A simple and facile method for the synthesis of aromatic tertiary amines by amination of fluoroarenes with secondary amines in the presence of n-butyllithium at room temperature was reported.
Lin, Yingyin,Li, Meng,Ji, Xinfei,Wu, Jingjing,Cao, Song
p. 1466 - 1472
(2017/02/18)

N-phenyl-piperazine a process for the preparation of
The invention discloses a preparation method of N-phenyl piperazine. The preparation method of the N-phenyl piperazine is characterized by comprising the following steps: by taking aniline and bis-(2-chloroethyl) amine hydrochloride as raw materials without any solvent, heating to the range of 160-250 DEG C so that the raw materials are fused and the two raw materials have a cyclization reaction in the fused state to generate N-phenyl piperazine hydrochloride; after the reaction is terminated, treating the reaction liquid by using an alkaline aqueous solution to obtain a coarse product; and performing reduced pressure distillation on the coarse product to obtain the product N-phenyl piperazine having the qualified purity. The preparation method is simple to operate, high in yield, relatively low in liquid waste and low in cost; the purity (HPLC (High Performance Liquid Chromatography)) of the N-phenyl piperazine is more than 99.5% and the yield is above 75%; and the preparation method is suitable for industrial production of the N-phenyl piperazine.
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Paragraph 0048-0049

(2017/02/09)

Indoline-2-ketone D3 receptor ligand and preparation method and application thereof
The invention discloses an indoline-2-ketone D3 receptor ligand, which is a compound as shown in the formula I or pharmaceutical salt thereof, wherein n=2 or 3; R represents H, 4-CH3, 2,3-diCH3, 2-CH3, 4-OCF3, 3-OCH3, 3,4-diCH3 or 4-Cl. In comparison with the prior art, the compound has a strong activity to a dopamine D3 receptor, is used in treating or preventing central nervous and metal diseases such as schizophrenia, Parkinson's disease, drug dependence and relapse, etc., can be used in neuroprotection, and is used as a tool drug for researching D3 receptor structure, function and diseases related to D3 receptor dysfunction.
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Paragraph 0049; 0050

(2016/10/08)

Hexahydropyrazine-quinoline D3 receptor ligand and preparation method and use
The present invention discloses a hexahydropyrazino-quinoline D3 receptor ligand, which is a compound shown as formula I or a pharmaceutically acceptable salt thereof, wherein n = 2,3 or 4; R is H, 4-Cl, 2,3-diCl, 4-CH3, 2,3-diCH3, 4-OCF3, 4-OCH3, 2-OCF3, 2,6-di CH3, 3,4-di CH3, 3-CF3, 4-Cl, 3-OCH3, 2-C2H5 or 2-CH3. Compared with the prior art, the compound has strong activity to a dopamine D3 receptor, and can be used for effective treatment of Parkinson's disease, schizophrenia, drug dependence and other central nervous and mental diseases.
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Paragraph 0052

(2016/10/08)

Charge-transfer-directed radical substitution enables para-selective C-H functionalization
Efficient C-H functionalization requires selectivity for specific C-H bonds. Progress has been made for directed aromatic substitution reactions to achieve ortho and meta selectivity, but a general strategy for para-selective C-H functionalization has remained elusive. Herein we introduce a previously unappreciated concept that enables nearly complete para selectivity. We propose that radicals with high electron affinity elicit arene-to-radical charge transfer in the transition state of radical addition, which is the factor primarily responsible for high positional selectivity. We demonstrate with a simple theoretical tool that the selectivity is predictable and show the utility of the concept through a direct synthesis of aryl piperazines. Our results contradict the notion, widely held by organic chemists, that radical aromatic substitution reactions are inherently unselective. The concept of radical substitution directed by charge transfer could serve as the basis for the development of new, highly selective C-H functionalization reactions.
Boursalian, Gregory B.,Ham, Won Seok,Mazzotti, Anthony R.,Ritter, Tobias
p. 810 - 815
(2016/07/29)

Application of nanoparticle mediated N-arylation of amines for the synthesis of pharmaceutical entities using vit-E analogues as amphiphiles in water
The first CuI-nanoparticle catalyzed inter and intramolecular N-arylation of amines using vitamin E analogues (TPGS) as amphipiles has been developed in water. Application of this transition metal-amphiphile C-N bond formation methodology is further extended for the synthesis of substituted indoles, bioactive natural product tryptanthrin and intermediates of pharmaceutical entities such as imatinib, nilotinib, selective D3 agonist/antagonist ligands, and oxacarbazepine. This journal is
Kumar, Atul,Bishnoi, Ajay Kumar
p. 20516 - 20520
(2015/03/30)

Cu(I) metal organic framework catalyzed C-C and C-N coupling reactions
DABCO (1,4-diazabicyclo[2.2.2]octane) based Cu(I) metal organic framework (here after represented as Cu(I)-MOF) catalyzed Sonogashira cross-coupling reaction of iodobenzene and phenylacetylene was conducted smoothly to afford diphenylacetylene in excellent yield under N2atmosphere. For comparative study, piperidine based Cu(I) clusters were also investigated. Among these catalysts, Cu(I)-MOF exhibited higher activity with good selectivity for the C-C cross-coupled product. Cu(I) catalysts investigated in this study exhibited similar activity in the C-C homo-coupling reaction of phenylacetylene in O2atmosphere. Application of these catalysts was extended in the C-N coupling reactions between phenylboronic acid and aromatic/aliphatic/heterocyclic amines. Cu(I)-MOF can be readily recovered from the reaction mixture and reused for several cycles without loss in the catalytic activity.
Rani, Poonam,Srivastava, Rajendra
p. 5256 - 5260
(2015/01/16)

4-Substituted-2-phenylquinazolines as inhibitors of BCRP
We investigated several 2-phenylquinazolines with different substitutions at position 4 for their BCRP inhibition. Compounds with phenyl ring attached via an amine-containing linker at position 4 were found to be potent inhibitors of BCRP. In general compounds with meta substitution of phenyl ring at position 4 were found to have higher inhibitory effect, compound 12 being the most potent and selective towards BCRP.
Juvale, Kapil,Wiese, Michael
p. 6766 - 6769,4
(2012/12/12)

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
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Page/Page column 58; 59

(2011/04/14)

Synthesis of novel piperazine phosphoramidate analogues of 2-arylquinolones
A series of novel piperazine phosphoramidate derivatives of 2-arylquinolones were synthesized to improve their physicochemical and biological properties through a facile phosphorylating reaction. Their structures were elucidated by NMR, ESI MS, and HRMS. Copyright Taylor & Francis Group, LLC.
Qu, Zhibo,Chen, Xiaolan,Qu, Lingbo,Yuan, Jinwei,Li, Huina,Zhao, Yufen
experimental part
p. 1516 - 1520
(2010/09/04)

4-Aryl piperazine and piperidine amides as novel mGluR5 positive allosteric modulators
Positive allosteric modulation of metabotropic glutamate receptor 5 (mGluR5) is regarded as a potential novel treatment for schizophrenic patients. Herein we report the synthesis and SAR of 4-aryl piperazine and piperidine amides as potent mGluR5 positive allosteric modulators (PAMs). Several analogs have excellent activity and desired drug-like properties. Compound 2b was further characterized as a PAM using several in vitro experiments, and produced robust activity in several preclinical animal models.
Xiong, Hui,Brugel, Todd A.,Balestra, Michael,Brown, Dean G.,Brush, Kelly A.,Hightower, Caprice,Hinkley, Lindsay,Hoesch, Valerie,Kang, James,Koether, Gerard M.,McCauley Jr., John P.,McLaren, Francis M.,Panko, Laura M.,Simpson, Thomas R.,Smith, Reed W.,Woods, James M.,Brockel, Becky,Chhajlani, Vijay,Gadient, Reto A.,Spear, Nathan,Sygowski, Linda A.,Zhang, Minli,Arora, Jalaj,Breysse, Nathalie,Wilson, Julie M.,Isaac, Methvin,Slassi, Abdelmalik,King, Megan M.
scheme or table
p. 7381 - 7384
(2011/02/26)

REAGENTS FOR BIOMOLECULAR LABELING, DETECTION AND QUANTIFICATION EMPLOYING RAMAN SPECTROSCOPY
The present disclosure provides isotopically substituted compounds of the formula (I): wherein T, U, V, W, X, Y, Z, R0, R3, R4, R5 and R6 are as defined in the detailed description. The method for detection and quantification using the same is also disclosed.
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Page/Page column 24-25

(2009/08/14)

Synthesis of lactosylated piperazinyl porphyrins and their hepatocyte-selective targeting
The aim of this work was the synthesis of a new family of lactosylated piperazinly porphyrins in which the galactoside piperazine moieties are linked to the tetra- and monophenyl ring by an amide bond. Two compounds were designed, synthesized, and characterized by 1H-nuclear magnetic resonance (1H-NMR), ultraviolet (UV)-visible, and matrix-assisted laser desorption/ionization (MALDI) mass spectra. The biological activity on cancer cells and the pharmacokinetics have also been evaluated, showing a very high liver-to-skin ratio and short retention time in tissues. It is suggested that such novel lactosylated piperazinyl porphyrins, as potential hepatocyte-selective targeting drugs, thus show promising activity in photodynamic therapy. Birkha?user Boston 2007.
Li, He-Ping,Cao, Zhong,Xiao, Hua-Wu
p. 28 - 38
(2008/04/01)

Unique spirocyclopiperazinium salt III: Further investigation of monospirocyclopiperazinium (MSPZ) salts as potential analgesics
Two novel classes of monospirocyclopiperazinium salts were designed, synthesized, and evaluated for their in vivo analgesic activities. Some interesting structure-activity relationships are revealed: (1) Spirocyclopiperazinium moiety is favorable to improve the analgesic activity; (2) The size and conformation of spirocyclopiperazinium moiety significantly affects the analgesic activity; (3) Phenylethyl group of 3d is a crucial pharmacophore. Among the compounds synthesized, 3d exhibited the most potent activity with low toxicity. Further antinociceptive mechanism studies of 3d showed that these compounds will be a new kind of analgesics.
Sun, Qi,Yue, Cai-Qin,Ye, Jia,Li, Chang-Ling,Cheng, Tie-Ming,Li, Run-Tao
p. 6245 - 6249
(2008/04/07)

Potent, selective, and orally active adenosine A2A receptor antagonists: Arylpiperazine derivatives of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines
Antagonism of the adenosine A2A receptor offers great promise in the treatment of Parkinson's disease. Employing the known pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine A2A antagonist SCH 58261 as a starting point, we identified the potent and selective (vs. A1) antagonist 11 h, orally active in the rat haloperidol-induced catalepsy model. We further optimized this lead to the methoxyethoxyethyl ether 12a (SCH 420814), which shows broad selectivity, good pharmacokinetic properties, and excellent in vivo activity.
Neustadt, Bernard R.,Hao, Jinsong,Lindo, Neil,Greenlee, William J.,Stamford, Andrew W.,Tulshian, Deen,Ongini, Ennio,Hunter, John,Monopoli, Angela,Bertorelli, Rosalia,Foster, Carolyn,Arik, Leyla,Lachowicz, Jean,Ng, Kwokei,Feng, Kung-I
p. 1376 - 1380
(2008/02/05)

Study on synthesis and biological activity of a galactosylated piperazinyl porphyrin
In order to obtain an carcinoma-selective drug, the synthesis and characterization of 5,10,15,20-tetra[4-(4′-galactosylpiperazinyl)phenyl]porphyrin (TGPP) is reported. The biological activity on cancer cells and the pharmacokinetics are also reported as preliminary results showing a very high liver to skin ratio and short retention time in tissues, and thus promising activity in photodynamic therapy.
Li, He-Ping
p. 6298 - 6301
(2007/10/03)

A general and convenient synthesis of N-aryl piperazines
A general and convenient synthesis of N-aryl piperazines from bis(2-chloroethyl)amine hydrochloride and a broad range of anilines in diethylene glycol monomethyl ether is described.
Liu, Kevin G.,Robichaud, Albert J.
p. 7921 - 7922
(2007/10/03)

SEROTONIN REUPTAKE INHIBITORS
A serotonin reuptake inhibitor which can be used in the treatment of depression and which has a decreased occurrence of unwanted side effects. The serotonin reuptake inhibitors are bi-functional organic molecules which combine serotonin transporter reuptake inhibition with serotonin (5-HT,such as 5-HT2A) receptor antagonism in one molecular entity. The serotonin-selective reuptake inhibitor (SSRI) homologue portion of the molecule shows an affinity to the serotonin reuptake transporter (SERT) and has antidepressant properties. The piperazine or piperidine portion of the molecule demonstrates an affinity to 5-HT receptors and restores the undesired side effects of SSRIs.
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Page/Page column 13-14

(2010/02/14)

Gram-scale synthesis of N-aryl- and N-aryl-N′-methylpiperazines on a novel, water-swellable, oxethane-linked poly(ethylene glycol) high-loading resin
A new methodology for the synthesis of N-arylpiperazines was developed using a poly(ethylene glycol)-derived solid support. The reactions proceeded in up to 60% overall yield over four steps. The scope and limitations of the method are discussed, as well as the utility of 13C gel-phase NMR spectroscopy for reaction monitoring. Georg Thieme Verlag Stuttgart.
Rudbeck, Hans Christian,Johannsen, Ib,Nielsen, Ole,Ruhland, Thomas,Sommer, Michael Bech,Tanner, David,Dancer, Robert
p. 3456 - 3462
(2007/10/03)

Ruthenium-Catalyzed Chemoselective N-Allyl Cleavage: Novel Grubbs Carbene Mediated Deprotection of Allylic Amines
A novel application of the Grubbs carbene complex has been discovered. The first examples of the catalytic deprotection of allylic amines with reagents other than palladium catalysts have been achieved through Grubbs carbene mediated reaction. Significantly, the catalytic system directs the reaction toward the selective deprotection of allylic amines (secondary as well as tertiary) in the presence of allylic ethers. A variety of substrates, including enantiomerically pure multifunctional piperidines, are also usable. The new method is more convenient, chemoselective, and operationally simple than the palladium-catalyzed method. The current mechanistic hypothesis invokes a nitrogen-assisted ruthenium-catalyzed isomerization, followed by hydrolysis of the enamine intermediate. We believe that the reactive species involved in the reaction may be an Ru-H species rather than the Grubbs carbene itself. Thus, the isomerization may occur according to the hydride mechanism. The synthetic utility of this ruthenium-catalyzed allyl cleavage is illustrated by the preparation of indolizidine-type alkaloids.
Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.
p. 5793 - 5799
(2007/10/03)

Sulfamato hydroxamic acid metalloprotease inhibitor
A sulfamato hydroxamic acid compound that, inter alia, inhibits matrix metalloprotease (mmp) activity is disclosed as are a process for preparing the same, intermediate compounds useful in those syntheses, and a treatment process that comprises administering a contemplated sulfamato hydroxamic acid compound in a MMP enzyme-inhibiting effective amount to a host having a condition associated with pathological matrix metalloprotease activity.
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(2008/06/13)

Palladium-catalyzed amination of aryl bromides using temperature-controlled microwave heating
Fast Palladium-catalyzed aminations of aryl bromides have been conducted in a non-inert reaction medium with temperature-controlled microwave heating. With a reaction time of 4 minutes at 130°C or 180°C, both electron-rich and electron-deficient aryl bromides reacted with various amines to provide fair to good yields of the corresponding secondary and tertiary anilines. As an example the amination of 4-bromobenzonitrile with imidazole is presented.
Wan, Yiqian,Alterman, Mathias,Hallberg, Anders
p. 1597 - 1600
(2007/10/03)

Nickel-catalysed selective N-arylation or N,N′-diarylation of secondary diamines
The selective synthesis of N-aryl or N,N′-diaryl piperazines and trimethylene(bis)piperidines from the corresponding diamines and aryl chlorides using a catalyst combination of Ni(0) associated to 2,2′-bipyridine is described. The Ni/2,2′-bipyridine catalyst is also effective for the sequential arylation of piperazine. The preparation of novel and unsymmetrical 1,4-diaryl piperazines is reported.
Brenner, Eric,Schneider, Rapha?l,Fort, Yves
p. 6913 - 6924
(2007/10/03)

Nickel(0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines
A general and simple nickel-catalyzed coupling of aryl chlorides and amines is reported. The scope and limitations of the coupling process using Ni(0), 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene, and NaO-t-Bu as base were investigated. Secondary cyclic and acyclic amines and anilines provided the arylamine coupling products in good to excellent yields. Compared to palladium-catalyzed aminations, this procedure offers an alternative route to N-substituted anilines starting from readily available aryl chlorides.
Desmarets, Christophe,Schneider, Raphael,Fort, Yves
p. 3029 - 3036
(2007/10/03)

Fused heterocyclic compounds and pharmaceutical applications thereof
The present invention relates to a fused heterocyclic compound of the formula (I) wherein each symbol is as defined in the specification, an optical isomer thereof, a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing a compound of the formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive, and a medicament containing a compound of the formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof. The compound of the present invention is a useful antipsychotic agent effective not only for positive symptoms centering on hallucination and delusion characteristic of the acute stage of schizophrenia, but also negative symptoms of apathy, abulia and autism. The inventive compound is expected to make a highly safe antipsychotic agent associated with less side effects, such as extrapyramidal symptoms and endocrine disturbance, which are observed when a conventional antipsychotic agent having a D2receptor blocking action is administered. Therefore, the inventive compound can be used as a therapeutic agent for the diseases such as schizophrenia.
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(2008/06/13)

A novel use of Grubbs' carbene. Application to the catalytic deprotection of tertiary allylamines
Figure presented The first examples accounting for the catalytic deprotection of allylic amines by using reagents different from palladium catalysts have been achieved via Grubbs' carbene-mediated reaction. The current mechanistic hypothesis invokes a nitrogen-assisted ruthenium-catalyzed isomerization, followed by hydrolysis of the enamine intermediate. We believe that an unprecedented mode of ring opening of the ruthena-cyclobutane was involved.
Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.,Aly, Moustafa F.
p. 3781 - 3784
(2007/10/03)

Nickel-mediated amination chemistry. Part 2: Selective N-arylation or N,N'-diarylation of piperazine
The 2,2'-bipyridine liganded Ni catalyst has revealed a good selectivity in the mono arylation of piperazine starting from aryl chlorides allowing a selective and efficient synthesis of N-arylpiperazines using stoichiometric amounts of reagents. The preparation of N,N'-diaryl substituted piperazines is also described. (C) 2000 Elsevier Science Ltd.
Brenner, Eric,Schneider, Rapha?l,Fort, Yves
p. 2881 - 2884
(2007/10/03)

Microwave assisted selective cleavage of sulfonates and sulfonamides in dry media
A simple and efficient method for the cleavage of Sulfonates and Sulfonamides has been achieved for the first time under microwave irradiation conditions using KF-Al2O3.
Sabitha, Gowravaram,Abraham, Sunny,Reddy, B. V. Subba,Yadav
p. 1745 - 1746
(2007/10/03)

Deprotection of sulfonamides using iodotrimethylsilane
The deprotection of sulfonamides is achieved under neutral conditions by reaction with iodotrimethylsilane in acetonitrile at reflux.
Sabitha, Gowravaram,Subba Reddy,Abraham, Sunny,Yadav
p. 1569 - 1570
(2007/10/03)

Process for producing heterocyclic aromatic amine or arylamine
A heterocyclic aromatic halide or an aryl halide is reacted with an amine compound in the presence of a base to give a heterocyclic aromatic amine or an arylamine, respectively. In this reaction, a catalyst comprising a palladium compound and a tertiary phosphine is used for the preparation of a heterocyclic aromatic amine, and a catalyst comprising a palladium compound and a trialkylphosphine is used for the preparation of an arylamine.
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(2008/06/13)

Scavenger assisted combinatorial process for preparing libraries of amides, carbamates and sulfonamides
This invention relates to a novel solution phase process for the preparation of amide, carbamate, and sulfonamide combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.
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(2008/06/13)

Substituted pyrazoles as novel selective ligands for the human dopamine D4 receptor
Two novel series of 3-(heterocyclylmethyl)pyrazoles have been synthesised and evaluated as ligands for the human dopamine D4 receptor. Compounds in series I (exemplified by 8k) have a phenyl ring joined to the 4-position of the pyrazole while those in series II (exemplified by 15j) have a 5-phenyl ring linked by a saturated chain to the 4-position of the pyrazole. Both series supplied compounds with excellent affinity for the human D4 and good selectivity over other dopamine receptors. Excellent selectivity over calcium, sodium, and potassium ion channels was also achieved. Copyright (C) 1997 Elsevier Science Ltd.
Bourrain, Sylvie,Collins, Ian,Neduvelil, Joseph G.,Rowley, Michael,Leeson, Paul D.,Patel, Smita,Patel, Shil,Emms, Frances,Marwood, Rosemarie,Chapman, Kerry L.,Fletcher, Alan E.,Showell, Graham A.
p. 1731 - 1743
(2007/10/03)

Synthesis of N-arylpiperazines from aryl halides and piperazine under a palladium tri-tert-butylphosphine catalyst
A Pd/P(t-Bu), catalyst system has revealed very high activity and selectivity for the amination of N-(hetero)aryl halides with unprotected piperazine. A wide variety of N-(hetero)arylpiperazines could be prepared using this catalyst. Turnover numbers up to 6400mol/mol have been obtained.
Nishiyama, Masakazu,Yamamoto, Toshihide,Koie, Yasuyuki
p. 617 - 620
(2007/10/03)

Microwave assisted rapid synthesis of 1-arylpiperazines
1-Arylpiperazines, an important class of compounds were synthesized rapidly under Microwave irradiation from diethanolamine and substituted anilines using Pollard's method of synthesis. The yields obtained were comparable with the conventional yields and drastic reduction in reaction time was observed.
Jaisinghani, Harsha G.,Chowdhury, Boudhayan Roy,Khadilkar
p. 1175 - 1178
(2007/10/03)

Fibrinogen receptor antagonists
Novel fibrinogen receptor antagonists of the formula: are provided in which the claimed compounds exhibit fibrinogen receptor antagonist activity, inhibit platelet aggregation and are therefore useful in modulating thrombus formation.
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(2008/06/13)

Rapid and efficient synthesis of 1-Arylpiperazines under microwave irradiation
1-Arylpiperazines, finding wide applicability in pharmaceuticals were synthesized easily under microwave irradiation from bis(2-chloroethyl)amine hydrochloride and substituted anilines without any solvent. The reaction time was just 1-3 mins. 1-Arylpiperazines were synthesized in 53 to 73% yields. Potent serotonin ligands like Trifluoromethylphenylpiperazine (TFMPP) and 3-Chlorophenylpiperazine (mCPP) were also prepared in just 1 min and 2 mins respectively.
Jaisinghani, Harsha G.,Khadilkar, Bhushan M.
p. 6875 - 6876
(2007/10/03)

Synthesis of arylpiperazines via nucleophilic aromatic substitution of (η6-fluoroarene)tricarbonylchromium complexes
A one-pot, high yield preparation procedure for the synthesis of arylpiperazines using a nucleophilic aromatic substitution of (η6-fluoroarene)tricarbonylchromium complexes (including those bearing electron donating groups) is described. A new, easy and fast decomplexation procedure, in DMSO as solvent, is also presented.
Perez, Michel,Potier, Pierre,Halazy, Serge
p. 8487 - 8488
(2007/10/03)

Formation of phenylpiperazines by a novel alumina supported bis-alkylation
The phenylpiperazine ring which could not be obtained by reacting aniline derivatives with bis(2-bromoethyl)-N-(ethoxycarbonyl)amine (1a) in a wide spectrum of solvents and temperatures was synthesized rapidly on solid support in high yield. By this approach the potent serotonin agonist TFMPP (2) was synthesized in 40 min. in 80% yield. The time scale of this reaction and the simplicity of the work-up match the requirements for short lived neurological radiopharmaceutical production.
Mishani, Eyal,Dence, Carmen S.,McCarthy, Timothy J.,Welch, Michael J.
p. 319 - 322
(2007/10/02)

Antiviral agents
Antiviral compounds (I): the symbols being as defined in the specification, are efficacious against infections caused by a variety of DNA viruses, RNA viruses and retroviruses. Other specified compounds also exhibit activity. The compounds have a wider spectrum of activity than known antiviral substances.
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(2008/06/13)

N-SUBSTITUTED DERIVATIVES OF (ALPHA)-MERCAPTO ALKYLAMINES, THEIR PREPARATION PROCESS AND THE INTERMEDIATES OBTAINED, THEIR USE AS MEDICAMENTS AND THE COMPOSITIONS CONTAINING THEM
Novel α-mercapto-alkylamines in all possible racemic, enantiomeric and diastereoisomeric forms of the formula STR1 wherein n, R 1, R 2, X, A, R 3A and R 4A are set forth in the claims and their non-toxic, pharmaceutically acceptable acid addition salts having excellent analgesic, psychotropic and enkephalinase inhibiting properties.
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(2011/02/21)