- Effect of N-Bound Organic Moiety in Dithiocarbamate (R2NCS-2) and trans Influence of Triphenylphosphine on NiS2PN Chromophore
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Three square planar Ni(II) complexes of the composition [Ni(bzcprdtc)2](1), [Ni(bzcprdtc)(NCS)(PPh3)](2) and [Ni(bzcprdtc)(PPh3)2]ClO4 (3)[(where bzcprdtc = N-benzyl-N-cyclopropyl-dithiocarbamate)] ha
- Sathiyaraj, Ethiraj,Valarmathi, Panneerselvam,Thirumaran, Subbiah,Ciattini, Samuele,Gupta, Vivek K.,Kant, Rajni
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Read Online
- Analgesic Properties of Opioid/NK1 Multitarget Ligands with Distinct in Vitro Profiles in Naive and Chronic Constriction Injury Mice
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The lower efficacy of opioids in neuropathic pain may be due to the increased activity of pronociceptive systems such as substance P. We present evidence to support this hypothesis in this work from the spinal cord in a neuropathic pain model in mice. Biochemical analysis confirmed the elevated mRNA and protein level of pronociceptive substance P, the major endogenous ligand of the neurokinin-1 (NK1) receptor, in the lumbar spinal cord of chronic constriction injury (CCI)-mice. To improve opioid efficacy in neuropathic pain, novel compounds containing opioid agonist and neurokinin 1 (NK1) receptor antagonist pharmacophores were designed. Structure-activity studies were performed on opioid agonist/NK1 receptor antagonist hybrid peptides by modification of the C-terminal amide substituents. All compounds were evaluated for their affinity and in vitro activity at the mu opioid (MOP) and delta opioid (DOP) receptors, and for their affinity and antagonist activity at the NK1 receptor. On the basis of their in vitro profiles, the analgesic properties of two new bifunctional hybrids were evaluated in naive and CCI-mice, representing models for acute and neuropathic pain, respectively. The compounds were administered to the spinal cord by lumbar puncture. In naive mice, the single pharmacophore opioid parent compounds provided better analgesic results, as compared to the hybrids (max 70% MPE), raising the acute pain threshold close to 100% MPE. On the other hand, the opioid parents gave poor analgesic effects under neuropathic pain conditions, while the best hybrid delivered robust (close to 100% MPE) and long lasting alleviation of both tactile and thermal hypersensitivity. The results presented emphasize the potential of opioid/NK1 hybrids in view of analgesia under nerve injury conditions.
- Starnowska, Joanna,Costante, Roberto,Guillemyn, Karel,Popiolek-Barczyk, Katarzyna,Chung, Nga N.,Lemieux, Carole,Keresztes, Attila,Van Duppen, Joost,Mollica, Adriano,Streicher, John,Vanden Broeck, Jozef,Schiller, Peter W.,Tourwé, Dirk,Mika, Joanna,Ballet, Steven,Przewlocka, Barbara
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Read Online
- Continuous flow heterogeneous catalytic reductive aminations under aqueous micellar conditions enabled by an oscillatory plug flow reactor
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Despite the fact that continuous flow processing exhibits well-established technical advances, aqueous micellar chemistry, a field that has proven extremely useful in shifting organic synthesis to sustainable water-based media, has mostly been explored under conventional batch-based conditions. This is particularly because of the fact that the reliable handling of slurries and suspensions in flow has been considered as a significant technical challenge. Herein, we demonstrate that the strategic application of an oscillatory plug flow reactor enables heterogeneous catalytic reductive aminations in aqueous micellar media enhancing mass transport and facilitating process simplicity, stability and scalability. The micellar flow process enabled a broad range of substrates, including amino acid derivatives, to be successfully transformed under reasonably mild conditions utilizing only very low amounts of Pd/C as a readily available heterogeneous catalyst. The preparative capabilities of the process along with the recyclability of the heterogenous catalyst and the aqueous reaction media were also demonstrated. This journal is
- ?tv?s, Sándor B.,Buchholcz, Balázs,Darvas, Ferenc,Kappe, C. Oliver,Novák, Zoltán,Sipos, Gellért,Wernik, Michaela
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supporting information
p. 5625 - 5632
(2021/08/16)
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- Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades
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The alkylation of amines with either alcohols or carboxylic acids represents a mild and safe alternative to the use of genotoxic alkyl halides and sulfonate esters. Here we report two complementary one-pot systems in which the reductive aminase (RedAm) from Aspergillus oryzae is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect N-alkylation reactions. The application of both approaches has been exemplified with respect to substrate scope and also preparative scale synthesis. These new biocatalytic methods address issues facing alternative traditional synthetic protocols such as harsh conditions, overalkylation and complicated workup procedures.
- Ramsden, Jeremy I.,Heath, Rachel S.,Derrington, Sasha R.,Montgomery, Sarah L.,Mangas-Sanchez, Juan,Mulholland, Keith R.,Turner, Nicholas J.
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p. 1201 - 1206
(2019/01/21)
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- Triazole compound, and application thereof in agriculture
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The invention provides a triazole compound, and an application thereof in agriculture, and concretely provides a compound represented by formula (I), a preparation method thereof, a composition containing the compound, and an application of the compound or the composition as a bactericide. R, X, R, R, n, R, R, R, R, R and R in the formula (I) are as defined in the description.
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Paragraph 0139-0144
(2019/12/29)
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- Direct Reductive Amination of Carbonyl Compounds with H2 Using Heterogeneous Catalysts in Continuous Flow as an Alternative to N-Alkylation with Alkyl Halides
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A general continuous-flow procedure for direct reductive amination of secondary and primary amines with aromatic and aliphatic aldehydes as well as ketones is reported. The use of hydrogen gas and commercially available Pt/C as a heterogeneous catalyst is a key. In addition to exhibiting an excellent functional group tolerance, this method allows the fast formation of C?N bonds without production of any hazardous chemical waste. Applications to the synthesis of key intermediates toward active pharmaceutical ingredients (Donepezil and Arformoterol/Tamsulosin) are also described. (Figure presented.).
- Laroche, Benjamin,Ishitani, Haruro,Kobayashi, Shū
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supporting information
p. 4699 - 4704
(2018/12/04)
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- Triazole compounds and their use in agriculture (by machine translation)
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The present invention provides a triazole compound and its application in agriculture; in particular, the invention provides compounds of formula (A) indicated by the compound and its preparation method; the composition containing these compounds and preparation and their use as fungicides; wherein R1 , R2 , R3 , W, R4 , R5 , R6 , R7 , R8 , R9 , Ra , Rb And in the event of x has the meanings given by the invention. (by machine translation)
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Paragraph 0386; 0387; 0388
(2018/11/04)
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- Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer
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Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.
- Huang, Yuan-Qiong,Song, Hong-Jian,Liu, Yu-Xiu,Wang, Qing-Min
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supporting information
p. 2065 - 2069
(2018/01/27)
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- Acidic solvent-free removal of amine-protecting diphenylmethyl groups in the presence of camphorsulfonic acid
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We developed novel reaction conditions for the removal of the diphenylmethyl group, which is one of the most important protecting groups for amines. The reaction was promoted by adding one equivalent of camphorsulfonic acid in aqueous media, and no acidic
- Yamagiwa, Noriyuki,Okabe, Takayuki,Suto, Yutaka,Iwasaki, Genji
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p. 1456 - 1458
(2017/11/04)
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- Direct Alkylation of Amines with Primary and Secondary Alcohols through Biocatalytic Hydrogen Borrowing
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The reductive aminase from Aspergillus oryzae (AspRedAm) was combined with a single alcohol dehydrogenase (either metagenomic ADH-150, an ADH from Sphingobium yanoikuyae (SyADH), or a variant of the ADH from Thermoanaerobacter ethanolicus (TeSADH W110A)) in a redox-neutral cascade for the biocatalytic alkylation of amines using primary and secondary alcohols. Aliphatic and aromatic secondary amines were obtained in up to 99 % conversion, as well as chiral amines directly from the racemic alcohol precursors in up to >97 % ee, releasing water as the only byproduct.
- Montgomery, Sarah L.,Mangas-Sanchez, Juan,Thompson, Matthew P.,Aleku, Godwin A.,Dominguez, Beatriz,Turner, Nicholas J.
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supporting information
p. 10491 - 10494
(2017/08/22)
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- Selective hydrogenation of nitriles to secondary amines catalyzed by a pyridyl-functionalized and alkenyl-tethered NHC-Ru(II) complex
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A set of Co(III) and Ru(II) compounds are synthesized bearing pyridyl-functionalized and alkenyl-tethered N-heterocyclic carbene (NHC) ligand (L1). [CoIII(L1)3](PF6)3 (1) was synthesized by the reaction of [L1H]PF6, Co(OAc)2.4H2O, K2CO3 in tetrahydrofuran (THF) under refluxing condition. [RuIIL1(η6-p-cymene)Cl]PF6 (2) was synthesized via transmetallation method. For both compounds, the NHC ligand chelates the metal through carbene carbon and pyridyl nitrogen whereas the butenyl unit remains free. Compound 2 hydrogenates organic nitriles efficiently providing selectively secondary amines. In the presence of external amines, unsymmetrical secondary amines are also obtained.
- Saha, Sayantani,Kaur, Mandeep,Singh, Kuldeep,Bera, Jitendra K.
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- Part 1: Notch-sparing γ-secretase inhibitors: The identification of novel naphthyl and benzofuranyl amide analogs
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γ-Secretase is one of two proteases directly involved in the production of the amyloid β-peptide (Aβ), which is pathogenic in Alzheimer's disease. Inhibition of γ-secretase to suppress the production of Aβ should not block processing of one of its alterna
- Lu, Dai,Wei, Han-Xun,Zhang, Jing,Gu, Yongli,Osenkowski, Pamela,Ye, Wenjuan,Selkoe, Dennis J.,Wolfe, Michael S.,Augelli-Szafran, Corinne E.
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p. 2129 - 2132
(2016/04/20)
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- Mild Metal-Free Hydrosilylation of Secondary Amides to Amines
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The combination of amide activation by Tf2O with B(C6F5)3-catalyzed hydrosilylation with TMDS constitutes a method for the one-pot reduction of secondary amides to amines under mild conditions. The method displays a broad applicability for the reduction of many types of substrates, and shows good compatibility and excellent chemoselectivity for many sensitive functional groups. Reductions of a multifunctionalized α,β-unsaturated amide obtained from another synthetic methodology, and a C-H functionalization product produced the corresponding amines in good to excellent yield. Chemoselective reduction of enantiomeric pure (ee >99%) tetrahydro-5-oxo-2-furaneamides yielded 5-(aminomethyl)dihydrofuran-2(3H)-ones in a racemization-free manner. The latter were converted in one pot to N-protected 5-hydroxypiperidin-2-ones, which are building blocks for the synthesis of many natural products. Further elaboration of an intermediate led to a concise four-step synthesis of -epi-pseudoconhydrine.
- Huang, Pei-Qiang,Lang, Qi-Wei,Wang, Yan-Rong
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p. 4235 - 4243
(2016/06/09)
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- Fe@Pd/C: An efficient magnetically separable catalyst for direct reductive amination of carbonyl compounds using environment friendly molecular hydrogen in aqueous reaction medium
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Direct reductive amination of carbonyl compounds with variety of amines has been reported by using magnetically separable Fe@Pd/C as an efficient catalyst in aqueous reaction medium. The developed methodology offers synthesis of various secondary and tertiary amines using different aldehydes and ketones with amines giving excellent yield. Moreover, the magnetically separable Fe@Pd/C catalyst was easily separated from reaction mixture and can be recycled for further reaction.
- Patil, Nilesh M.,Bhanage, Bhalchandra M.
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p. 182 - 189
(2015/03/30)
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- Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy
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A short entry to substituted azocanes by a Rh-catalyzed cycloaddition-fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible.
- Shaw, Megan H.,Croft, Rosemary A.,Whittingham, William G.,Bower, John F.
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supporting information
p. 8054 - 8057
(2015/07/15)
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- Ultrasound-assisted solventless synthesis of amines by in situ oxidation/reductive amination of benzyl halides
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Ultrasound-assisted solventless oxidation/reductive amination of benzyl halides was developed as a facile, efficient, and environmental friendly method toward N-alkylated amines. Aldehydes were formed in situ by oxidation of organic halides with N-methylmorpholine N-oxide (NMO), followed by direct reductive amination with amines using sodium borohydride and montmorillonite K-10 catalyst as the reducing system. This green and simple procedure enables N-alkylated amines to be prepared in good to excellent yields with high selectivity of the monoalkylation. This journal is the Partner Organisations 2014.
- Khumraksa, Bannarak,Phakhodee, Wong,Pattarawarapan, Mookda
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p. 20454 - 20458
(2014/06/09)
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- Reductive detriflylation of N-triflylamides with Red-Al
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Reduction of cis-N-triflylaziridines with 10 equiv of Red-Al in toluene at-40 to 0 °C selectively afforded corresponding deprotected parent aziridines in good to high yields. N,N-Dialkyltriflylamides were also successfully cleaved under similar reaction conditions.
- Miyamoto, Kazunori,Hoque, Md. Mahbubul,Ogasa, Sayaka
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p. 8317 - 8320
(2013/01/15)
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- Electrochemical cleavage of sulfonamides: An efficient and tunable strategy to prevent β-fragmentation and epimerization
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The electrochemical reduction of sensitive sulfonamides is described. The addition of a benzoyl group on the nitrogen atom facilitates the reductive cleavage of sulfonamides preventing β-fragmentation and epimerization. This strategy was successfully applied to the cyclopropylamine and to α-amino stannanes.
- Viaud, Pierre,Coeffard, Vincent,Thobie-Gautier, Christine,Beaudet, Isabelle,Galland, Nicolas,Quintard, Jean-Paul,Le Grognec, Erwan
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scheme or table
p. 942 - 945
(2012/03/26)
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- Mild electrochemical deprotection of N-phenylsulfonyl N-substituted amines derived from (R)-phenylglycinol
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The electrochemical reduction of N-phenylsulfonyl N-substituted amines in a protic medium under constant cathodic potential was found to be a mild desulfonylation method, which is able to challenge the chemical ones. The influence of the nature of the N-substituents was considered in order to clarify the mechanistic aspects and to evaluate the scope of the method. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Coeffard, Vincent,Thobie-Gautier, Christine,Beaudet, Isabelle,Le Grognec, Erwan,Quintard, Jean-Paul
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p. 383 - 391
(2008/09/18)
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- RENIN INHIBITORS
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The present invention relates to novel renin inhibitors of the general Formula (I), and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds. These novel renin inhibitors are used in treating cardiovascular events and renal insufficiency.
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Page/Page column 45
(2008/06/13)
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- MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 6: Exploration of aromatic substituents
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A series of 4-oxo-4H-pyrido[1,2-a]pyrimidine derivatives, derivatized at the 2-position with aromatic substituents, were synthesized by the Suzuki cross-coupling method and evaluated for their ability to potentiate the activity of the fluoroquinolone levo
- Yoshida, Ken-ichi,Nakayama, Kiyoshi,Yokomizo, Yoshihiro,Ohtsuka, Masami,Takemura, Makoto,Hoshino, Kazuki,Kanda, Hiroko,Namba, Kenji,Nitanai, Hironobu,Zhang, Jason Z.,Lee, Ving J.,Watkins, William J.
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p. 8506 - 8518
(2008/02/05)
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- TACHYKININ RECEPTOR ANTAGONISTS
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The present invention relates to selective NK-1 receptor antagonists of Formula (I) or a pharmaceutically acceptable salt thereof, for the treatment of disorders associated with an excess of tachykinins.
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- o-Iodoxybenzoic Acid (IBX) as a Viable Reagent in the Manipulation of Nitrogen- and Sulfur-Containing Substrates: Scope, Generality, and Mechanism of IBX-Mediated Amine Oxidations and Dithiane Deprotections
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o-Iodoxybenzoic acid (IBX), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the dehydrogenation of amines in addition to facilitating the oxidative cleavage of dithioacetals and dithioketals. Through the development of relevant IBX-based protocols, a plethora of useful synthetic intermediates, including imines, oximes, ketones, and aromatic N-heterocycles, were found to be readily accessible under notably mild conditions. Further investigation of these transformations led to the elucidation of valuable mechanistic details, resulting in the conclusion that they proceed via ionic rather than single electron transfer (SET) pathways.
- Nicolaou,Mathison, Casey J. N.,Montagnon, Tamsyn
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p. 5192 - 5201
(2007/10/03)
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- Synthesis of C-aryl-N-cyclopropylnitrones
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Synthesis of C-aryl-N-cyclopropylnitrones is described. Preparations were performed either by condensation of the appropriate aldehyde with N-cyclopropyl-hydroxylamine, or oxidation of N-substituted N-cyclopropylamines with sodium tungstate/hydrogen perox
- Vukics, Krisztina,Tarkanyi, Gabor,Dravecz, Ferenc,Fischer, Janos
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p. 3419 - 3425
(2007/10/03)
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- Steric factors in the gas phase elimination kinetics of ethyl N-benzyl-N-cyclopropylcarbamate and ethyl diphenylcarbamate
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The elimination kinetics of ethyl N-benzyl-N-cyclopropylcarbamate and ethyl diphenylcarbamate were investigated over the temperature range of 349.9-440.0°C and the pressure range of 31-106 Torr. These reactions have been found to be homogeneous, unimolecular, and obey a first-order rate law. The products are ethylene, carbon monoxide, and the corresponding secondary amine. The rate coefficient is expressed by the following Arrhenius equations: For ethyl N-benzyl-N-cyclopropylcarbamate log k1 (s-1) = (1 2.94 ± 0.09) - (198.5 ± 0.9) kJ mol-1 (2.303RT)-1. For ethyl diphenylcarbamate log k1(S-1 = (12.91 ± 0.18) - (208.2 ± 2.4) kJ mol-1 (2.303RT)-1. The presence of phenyl and bulky groups at the nitrogen atom of the ethylcarbamate showed a decrease in the rate of elimination. Steric factor may be operating during the process of decomposition of these substrates. These reactions appear to undergo a semipolar six-membered cyclic transition type of mechanism.
- Luiggi,Dominguez,Rotinov,Herize,Cordova,Chuchani
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- N1,N10-Ethylene-bridged high-potential flavins: Synthesis, characterization, and reactivity
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N1,N10-Ethyleneisoalloxazinium chloride and its 8-Cl-, 7-CF3-, and 3-CH3-7-CF3-substituted analogs were synthesized for the purpose of exhibiting thermal reactivity with organic substrates. The new flavins were characterized spectroscopically and electrochemically, and were found to react with amines, thiols, and phenylhydrazine, the latter case exhibiting catalytic aerobic recycling. Reactions of aliphatic benzylic and cyclopropyl amines with the 7-CF3 analog were also compared to their oxidations by tris(phenanthroline)iron(III). All reactions of the flavinium salts appear to occur through heterolytic rather than homolytic mechanisms.
- Li, Wen-Shan,Zhang, Nanjing,Sayre, Lawrence M.
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p. 4507 - 4522
(2007/10/03)
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- N-Alkyl-N-Cyclopropylanilines as Mechanistic Probes in the Nitrosation of N,N-Dialkyl Aromatic Amines
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A group of N-cyclopropyl-N-alkylanilines has been synthesized, and their reaction with nitrous acid in aqueous acetic acid at 0°C was examined. All compounds reacted rapidly to produce the corresponding N-alkyl-N-nitrosoaniline by specific cleavage of the cyclopropyl group from the nitrogen. The transformations were unaffected by the nature of the alkyl substituent (Me, Et, iPr, Bn). The reaction of 4-chloro-N-2-phenylcyclopropyl-N-methylaniline with nitrous acid gave 4-chloro-N-methyl-N-nitrosoaniline (76%), cinnamaldehyde (55%), 3-phenyl-5-hydroxyisoxazoline (26%), and 5-(N-4-chlorophenylmethylamino)-3-phenylisoxazoline (8%). Both the selective cleavage of the cyclopropyl group from the aromatic amine nitrogen and nature of the products derived from the cyclopropane ring support a mechanism involving the formation of an amine radical cation. This step is followed by rapid cyclopropyl ring opening to produce an iminium ion with a C-centered radical which either combines with NO or is oxidized.
- Loeppky, Richard N.,Elomari, Saleh
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- β-lactam derivatives as inhibitors of human cytomegalovirus protease
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The development of novel monobactam inhibitors of HCMV protease incorporating a carbon side chain at C-4 and a urea function at N-1 is described. Substitution with small groups at the C-3 position of the β- lactam ring gave an increase in enzymatic activity and in stability; however, a lack of selectivity against other serine proteases was noted. The use of both triand tetrasubstituted urea functionalities gave effective inhibitors of HCMV protease. Benzyl substitution of the urea moiety was beneficial, especially when strong electron-withdrawing groups where attached at the para position. Modest antiviral activity was found in a plaque reduction assay.
- Yoakim, Christiane,Ogilvie, William W.,Cameron, Dale R.,Chabot, Catherine,Guse, Ingrid,Haché, Bruno,Naud, Julie,O'Meara, Jeff A.,Plante, Raymond,Déziel, Robert
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p. 2882 - 2891
(2007/10/03)
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- Latent inhibitors of aldehyde dehydrogenase as alcohol deterrent agents
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A series of compounds structurally related to pargyline (N-methyl-N-propargylbenzylamide) were synthesized with the propargyl group replaced by a cyclopropyl, allyl, or 2,2,2-trichloroethyl group and, additionally in several cases, with the methyl group r
- Nagasawa,Elberling,DeMaster
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p. 1335 - 1339
(2007/10/02)
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- Synthesis and characterization of 5H-1,3-dioxolo[4,5-f]indoleethylamines
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Twelve new N,N-dialkylated-5,6-methylenedioxytryptamines and N-cyclopropyl-5,6-methylenedioxytryptamine were prepared as hybrids of known psychoactive phenylethylamines and tryptamines. Novel, more convenient synthesis of N-methyl- and N-benzylcyclopropyl
- Grotjahn
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p. 1031 - 1036
(2007/10/02)
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