- Synthesis of novel 1,3-thiazin-4-ones by acetylene diester cyclization and their anticancer activities
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A novel series of 1,3-thiazin-4-one derivatives containing a piperidyl ring (7–16) were designed and synthesized efficiently by thioamide and acetylene diester cyclization reaction via aminolysis of the ester group and the elimination of an alcohol molecu
- Anand, Selvam Athavan Alias,Loganathan, Chandrasekaran,Thomas, Nisha Susan,Saravanan, Kuppusamy,Alphonsa, Antony Therasa,Kabilan, Senthamaraikannan
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- Metal-free Photochemical Atom Transfer Radical Addition (ATRA) of BrCCl3 to Alkenes
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A simple, photochemical, and metal-free protocol for the atom transfer radical addition (ATRA) of bromotrichloromethane onto various alkenes is described. Among a range of organic molecules, phenylglyoxylic acid proved to be the most suitable photoinitiator to promote a sustainable process for the addition of bromotrichloromethane to olefins. This photochemical atom transfer radical protocol can be expanded into a wide substrate scope of aliphatic olefins bearing various functional groups, leading to the corresponding products in good to excellent yields.
- Nikitas, Nikolaos F.,Voutyritsa, Errika,Gkizis, Petros L.,Kokotos, Christoforos G.
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supporting information
p. 96 - 101
(2021/01/04)
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- Alkenylation and Arylation of Peptides via Ni-Catalyzed Reductive Coupling of α- C-Tosyl Peptides with Csp2Triflates/Halides
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A Ni-catalyzed reductive cross-coupling between α-C-tosyl peptides and Csp2 triflates/halides has been developed. This protocol enables the formation of various unnatural di- and tripeptides containing vinyl and aryl side chains, and it expands the applications of Ni-catalyzed reductive cross-coupling in late-stage diversification of peptides.
- Chen, Yunrong,Gong, Hegui,Ma, Guobin,Qian, Qun,Song, Yanhong,Sun, Deli,Tao, Xianghua
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supporting information
p. 7418 - 7422
(2021/10/12)
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- Synthesis of α-Quaternary Bicyclo[1.1.1]pentanes through Synergistic Organophotoredox and Hydrogen Atom Transfer Catalysis
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Bicyclo[1.1.1]pentanes (BCPs) are important in drug design as sp3-rich bioisosteres of arenes and tert-butyl groups; however, the preparation of BCPs with adjacent quaternary carbons is barely known. We report a facile synthesis of α-quaternary BCPs using organophotoredox and hydrogen atom transfer catalysis in which α-keto radicals, generated through oxidation of β-ketocarbonyls, undergo efficient addition to [1.1.1]propellane. The BCP products can be transformed into a variety of useful derivatives, including enantioenriched BCPs featuring α-quaternary stereocenters.
- Anderson, Edward A.,Frank, Nils,Mousseau, James J.,Nugent, Jeremy,Sterling, Alistair J.
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supporting information
p. 8628 - 8633
(2021/11/17)
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- Cobalt-Catalyzed Aerobic Oxidative Cleavage of Alkyl Aldehydes: Synthesis of Ketones, Esters, Amides, and α-Ketoamides
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A widely applicable approach was developed to synthesize ketones, esters, amides via the oxidative C?C bond cleavage of readily available alkyl aldehydes. Green and abundant molecular oxygen (O2) was used as the oxidant, and base metals (cobalt and copper) were used as the catalysts. This strategy can be extended to the one-pot synthesis of ketones from primary alcohols and α-ketoamides from aldehydes.
- Li, Tingting,Hammond, Gerald B.,Xu, Bo
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supporting information
p. 9737 - 9741
(2021/05/31)
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- Sequential Suzuki-Miyaura Coupling/Lewis Acid-Catalyzed Cyclization: An Entry to Functionalized Cycloalkane-Fused Naphthalenes
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Functionalized angular cycloalkane-fused naphthalenes were prepared using a two-step process involving a Pd-catalyzed Suzuki-Miyaura coupling of aryl pinacol boronates and vinyl triflates followed by a boron trifluoride etherate-catalyzed cycloaromatization.
- Mahecha-Mahecha, Camilo,Lecornué, Frédéric,Akinari, Sumita,Charote, Thomas,Gamba-Sánchez, Diego,Ohwada, Tomohiko,Thibaudeau, Sébastien
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supporting information
p. 6267 - 6271
(2020/09/02)
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- Synthesis of α-enaminones from cyclic ketones and anilines using oxoammonium salt as an oxygen transfer reagent
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A convenient and straightforward transformation of cyclic ketones with anilines at room temperature has been developed using oxoammonium salt TEMPO+PF6- as an oxidant. This method enabled the synthesis of a broad range of α-enaminones. The 18O-labeling experiment demonstrated that oxoammonium salt served as the oxygen transfer reagent.
- Xu, Biping,Shang, Yaping,Jie, Xiaoming,Zhang, Xiaofeng,Kan, Jian,Yedage, Subhash Laxman,Su, Weiping
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supporting information
p. 1827 - 1831
(2020/04/07)
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- Selective C-H Olefination of Indolines (C5) and Tetrahydroquinolines (C6) by Pd/S,O-Ligand Catalysis
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Herein, we report a highly selective C-H olefination of directing-group-free indolines (C5) and tetrahydroquinolines (C6) by Pd/S,O-ligand catalysis. In the presence of the S,O-ligand, a wide range of challenging indolines, tetrahydroquinolines, and olefins was efficiently olefinated under mild reaction conditions. The synthetic potential of this methodology was demonstrated by the efficient olefination of several indoline-based natural products.
- Jia, Wen-Liang,Westerveld, Nick,Wong, Kit Ming,Morsch, Thomas,Hakkennes, Matthijs,Naksomboon, Kananat,Fernández-Ibá?ez, M. ángeles
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supporting information
p. 9339 - 9342
(2019/11/21)
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- Copper-Catalyzed One-Pot Borylative Aldolisation β-Fluoride Elimination for the Formal Addition of Acrylates to Carbonyl Moieties
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Herein, we report the copper-catalyzed domino borylation/aldolisation of methyl 2-fluoroacrylate with carbonyl compounds followed by an elimination to give Morita–Baylis–Hillman (MBH) analogues. The optimal conditions described were shown to be compatible
- Rasson, Corentin,Stouse, Adrien,Boreux, Arnaud,Cirriez, Virginie,Riant, Olivier
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supporting information
p. 9234 - 9237
(2018/06/04)
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- Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes
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(Chemical Equation Presented) "Cu-CF3" species have been used historically for a broad spectrum of nucleophilic trifluoromethylation reactions. Although recent advancements have employed ligands to stabilize and harness the reactivity of this key organometallic intermediate, the ability of a ligand to differentiate a regiochemical outcome of a Cu-CF3-mediated or -catalyzed reaction has not been previously reported. Herein, we report the first example of a Cu-catalyzed trifluoromethylation reaction in which a ligand controls the regiochemical outcome. More specifically, we demonstrate the ability of bipyridyl-derived ligands to control the regioselectivity of the Cu-catalyzed nucleophilic trifluoromethylation reactions of propargyl electrophiles to generate (trifluoromethyl)allenes. This method provides a variety of di-, tri-, and tetrasubstituted (trifluoromethyl)allenes, which can be further modified to generate complex fluorinated substructures.
- Ambler, Brett R.,Peddi, Santosh,Altman, Ryan A.
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supporting information
p. 2506 - 2509
(2015/05/27)
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- Discovery of tetrahydropyrido[4,3-d]pyrimidine derivatives for the treatment of neuropathic pain
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A series of tetrahydropyridopyrimidine derivatives were synthesized and evaluated for neurotoxicity and peripheral analgesic activity followed by assessment of antiallodynic and antihyperalgesic potential in two peripheral neuropathic pain models, the chronic constriction injury (CCI) and partial sciatic nerve ligation (PSNL). Compounds (4b and 4d) exhibiting promising efficacies in four behavioral assays of allodynia and hyperalgesia (spontaneous pain, tactile allodynia, cold allodynia and mechanical hyperalgesia) were quantified for their ED50 values (15.12-65.10 mg/kg). Studies carried out to assess the underlying mechanism revealed that the compounds suppressed the inflammatory component of the neuropathic pain and prevented oxidative and nitrosative stress.
- Sharma, Monika,Deekshith, Vanamala,Semwal, Arvind,Sriram, Dharmarajan,Yogeeswari, Perumal
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- Novel 3,5-bis(arylidiene)-4-piperidone based monocarbonyl analogs of curcumin: Anticancer activity evaluation and mode of action study
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A series of eighteen novel 3,5-bis(arylidiene)-4-piperidone based symmetrical monocarbonyl analogs of curcumin were synthesised and a subset was screened by National Cancer Institute (NCI), USA for their anticancer activity. Dose-response studies and the
- Thakur, Anuj,Manohar, Sunny,Vélez Gerena, Christian E.,Zayas, Beatriz,Kumar, Vineet,Malhotra, Sanjay V.,Rawat, Diwan S.
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p. 576 - 586
(2014/05/06)
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- CURCUMIN ANALOGS AND METHODS OF MAKING AND USING THEREOF
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Compounds having Formula I or II, and methods of making and using thereof, are described herein:
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Page/Page column 64
(2014/02/16)
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- Synthesis and application of N-tosyl piperidinyl-containing α-aminophosphonates
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A series of novel (4′-tosyl) piperidin-4-yl containing α-aminophosphonates were synthesized by a one-pot reaction, efficiently catalyzed by magnesium perchlorate, under solvent-free conditions from 1-tosylpiperidin-4-one, substituted aromatic amines, and diethyl phosphite (DEP). The synthesized compounds were characterized by IR, 1H NMR, 13C NMR, 31P NMR, and HRMS spectroscopy. A single-crystal X-ray structure of diethyl 4-(2-chlorophenyl) amino-1-(4-methylbezenesulfonyl) piperidin-4-yl-phosphonate (2a) was obtained, and some of the title compounds displayed insecticidal activities against Plutella xylostella. Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional figures and tables.
- Jiang, Zhifu,Zhao, Jian,Gao, Beibei,Chen, Shuo,Qu, Wenyan,Mei, Xiangdong,Rui, Changhui,Ning, Jun,She, Dongmei
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p. 1026 - 1037
(2013/09/02)
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- Synthesis and antimalarial-activity evaluation of tetraoxane-triazine hybrids and spiro[piperidine-4,3′-tetraoxanes]
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A series of tetraoxane-triazine hybrids and spiro[piperidine-4,3′- tetraoxanes] have been synthesized, and all the compounds were screened for in vitro antimalarial activity against chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plas
- Kumar, Nitin,Khan, Shabana I.,Rawat, Diwan S.
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scheme or table
p. 1181 - 1197
(2012/09/22)
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- The Piloty-Robinson reaction of N-substituted piperidin-4-one azines. A novel route for the synthesis of 3,6-diazacarbazole
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The possibility of preparing 1,2,3,4,6,7,8,9-octahydro-5H-pyrrolo[3,2-c:4, 5-c']dipyridines using the Piloty-Robinson reaction has been studied under various conditions. A novel method is proposed for the synthesis of the aromatic 3,6-diazacarbazole (5H-pyrrolo[3,2-c:4,5-c']dipyridine) from 2,8-dibenzoyl-1,2,3,4,6,7,8,9-octahydro-5H-pyrrolo[3,2-c:4,5-c']dipyridine obtained for the first time by the Piloty- Robinson method under thermal conditions.
- Alekseyev,Kurkin,Yurovskaya
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experimental part
p. 584 - 596
(2012/01/12)
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- Synthesis of 5-azaindoles via a cycloaddition reaction between nitriles and donor-acceptor cyclopropanes
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(Figure Presented) A new method for the synthesis of 5-azaindole derivatives is reported. A [3+2] dipolar cycloaddition between nitriles and a 3,4-cyclopropanopiperidine followed by SeO2 oxidation affords the target compounds in moderate to excellent yields. The divergent nature and cost effectiveness of this method makes it very suitable for combinatorial applications in the pharmaceutical industry.
- Moustafa, Mahmoud M. Abd Rabo,Pagenkopf, Brian L.
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supporting information; scheme or table
p. 3168 - 3171
(2010/09/10)
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- COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF
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Provided herein are compounds and methods of synthesis thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, psychiatric disorders, neuromuscular disorders, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds provided herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.
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Page/Page column 230
(2010/11/03)
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- NOVEL ANALGESIC THAT BINDS FILAMIN A
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A compound, composition and method are disclosed that can provide analgesia. A contemplated compound has a structure that corresponds to Formula I, wherein R1 and R2 are substituents, and n, W, X and Y are defined within.
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Page/Page column 19-20
(2010/12/29)
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- Addition of lithiated methoxyallene to aziridines - A novel access to enantiopure piperidine and β-amino acid derivatives
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Addition of lithiated methoxyallene to aziridine derivatives provided the expected primary addition products. The less substituted carbon of the aziridine ring was attacked selectively. The primary adducts could be converted to enantiopure piperidine deri
- Prisyazhnyuk, Vladimir,Jachan, Matthias,Bruedgam, Irene,Zimmer, Reinhold,Reissig, Hans-Ulrich
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experimental part
p. 1069 - 1080
(2010/04/26)
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- SOLUBLE EPOXIDE HYDROLASE INHIBITORS
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Disclosed are alpha keto amide and alpha hydroxy amide compounds and compositions that inhibit soluble epoxide hydrolase (sEH), methods for preparing the compounds and compositions, and methods for treating patients with such compounds and compositions. The compounds, compositions, and methods are useful for treating a variety of sEH mediated diseases, including hypertensive, cardiovascular, inflammatory, pulmonary, and diabetic-related diseases.
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Page/Page column 99
(2008/12/06)
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- Nitrostated and nitrosylated prostaglandins, compositions and methods of use
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The present invention describes novel nitrosated and/or nitrosylated prostaglandins, and novel compositions comprising at least one nitrosated and/or nitrosylated prostaglandin, and, optionally, at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase, and/or at least one vasoactive agent. The present invention also provides novel compositions comprising at least one prostaglandin and at least one S-nitrosothiol compound, and, optionally, at least one vasoactive agent. The prostaglandin is preferably a prostaglandin E1 compound, more preferably alprostadil, and the S-nitrosothiol compound is preferably S-nitrosoglutathione. The present invention also provides methods for treating or preventing sexual dysfunctions in males and females, for enhancing sexual responses in males and females, and for treating or preventing cerebrovascular disorders, cardiovascular disorders, benign prostatic hyperplasia (BPH), glaucoma, peptic ulcers or for inducing abortions. The compounds and/or compositions of the present invention can also be provided in the form of a pharmaceutical kit.
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Page/Page column 40
(2008/06/13)
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- New synthesis of 3-arylpyrrolines
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We present an easy and straightforward synthesis of 3-arylpyrrolines 4a-g by repeated treatment of 4-aryl-1,2,5,6-tetrahydropyridines 2a-g with m-chloroperoxybenzoic acid (MCPBA) and boron trifluoride etherate (BF 3-OEt2). The transformation proceeds via epoxidation, ring contraction, Baeyer-Villiger oxidation and elimination reaction and affords 3-arylpyrrolines 4a-g with 61-70% yield. This facile strategy was also used to synthesize racemic baclofen (6).
- Chang, Meng-Yang,Pai, Chun-Li,Kung, Yung-Hua
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p. 855 - 859
(2007/10/03)
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- CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines
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A CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines 2Aa-Be to β-amino carbonyl compounds 3Aa-Be and 4Aa-Be in different ratios is described. This facile strategy was also used to synthesize racemic fluoxetine (5).
- Chang, Meng-Yang,Lin, Chun-Yu,Pai, Chun-Li
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p. 2565 - 2568
(2007/10/03)
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- Catalytic enantioselective conjugate addition of dialkylzinc reagents to N-substituted-2,3-dehydro-4-piperidones
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The first, highly enantioselective, copper/phosphoramidite-catalyzed conjugate addition of dialkylzinc reagents to N-substituted 2,3-dehydro-4- piperidones is described. The Royal Society of Chemistry 2005.
- Sebesta, Radovan,Pizzuti, Maria Gabriella,Boersma, Arnold J.,Minnaard, Adriaan J.,Feringa, Ben L.
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p. 1711 - 1713
(2007/10/03)
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- Synthesis of heteroarylpiperazines and heteroarylbipiperidines with a restricted side chain and their affinities for 5-HT1A receptor
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Heteroarylpiperazine and heteroarylbipiperidine derivatives, bearing a 4-piperidine ring instead of an alkylamino side chain to give the semi-rigidity, were prepared and evaluated for their abilities to displace [3H] 8-OH-DPAT binding to the rat hippocampal synaptic membranes. These compounds showed low to moderate affinities for 5-HT1A receptor, with Ki values ranging from 6912 nM to 232 nM. Of these compounds, 8 b and 15 e exhibited the best affinities for 5-HT1A receptor with Ki values of 232 nM and 338 nM, respectively.
- Yoo, Kyung Ho,Choi, Hyun Sik,Kim, Dong Chan,Shin, Kye Jung,Kim, Dong Jin,Song, Yun Seon,Jin, Changbae
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p. 208 - 215
(2007/10/03)
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- Spiro and dispiro 1,2,4-trioxolane antimalarials
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A means and method for treating malaria using a spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl or spiropiperidyl ring on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably functionalized or substituted at the 4-position or a spiropiperidyl ring that is functionalized or substituted at the nitrogen atom. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.
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- Facile and Clean Oxidation of Alcohols in Water Using Hypervalent Iodine (III) Reagents
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The facile and efficient oxidation of various alcohols such as benzylic alcohols, primary alcohols, secondary alcohols, and diols in water using the hypervalent iodine(III) reagent, iodosobenzene (PhI=O), with KBr is described. Electrospray ionization (ESI) mass spectrometric studies on the behavior of PhI=O-KBr in aqueous solution suggested that these reactions are induced by the formation of highly reactive iodine species [PhI(Br)nO-]. Further development to recyclable polymer-supported iodine(III) reagent extends the utility of this reaction to afford an environmentally benign method.
- Tohma, Hirofumi,Maegawa, Tomohiro,Takizawa, Shinobu,Kita, Yasuyuki
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p. 328 - 337
(2007/10/03)
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- Facile and clean oxidation of alcohols in water using hypervalent iodine(III) reagents
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An environmentally benign oxidation of alcohols in water using iodosobenzene (PhI=O) or a polymer-supported (diacetoxyiodo)benzene (PSDIB) with KBr has been achieved (see scheme). This method results in the catalytic activation of a variety of sluggishly reactive and/or sparsely soluble hypervalent iodine reagents in water under neutral conditions.
- Tohma, Hirofumi,Takizawa, Shinobu,Maegawa, Tomohiro,Kita, Yasuyuki
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p. 1306 - 1308
(2007/10/03)
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- Clean six-step synthesis of a piperidino-thiomorpholine library using polymer-supported reagents
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Polymer-supported reagents and other solid sequestering agents may be used to generate a library of piperidino-thiomorpholine derivatives without any chromatographic purification steps.
- Habermann, Joerg,Ley, Steven V.,Scott, James S.
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p. 3127 - 3130
(2007/10/03)
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