cas 3235-82-3, ETHYL MORPHOLINOACETATE, 98

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Synthesis of novel Schiff bases and azol-β-lactam derivatives starting from morpholine and thiomorpholine and investigation of their antitubercular, antiurease activity, acethylcolinesterase inhibition effect and antioxidant capacity
In this study, new Schiff bases and β-lactam derivatives containing morpholine and thio morpholine nuclei were synthesized. Antimicrobial, antioxidant, antimicrobial and antioxidant properties of all synthesized compounds were investigated and highly effe
Cebeci, Y?ld?z Uygun,Bayrak, Hacer,?irin, Yakup
(2019)
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Cyclobutadiene cobalt complexes as catalysts for insertion of diazo compounds into X–H bonds
Novel cyclobutadiene cobalt complex with labile naphthalene ligand [(C4Et4)Co(C10H8)]PF6 catalyzes the insertion of ethyl diazoacetate into X–H bonds giving the corresponding products in 15–75% yields
Perekalin, Dmitry S.,Shvydkiy, Nikita V.
p. 350 - 351
(2021/06/07)

Selective carbene transfer to amines and olefins catalyzed by ruthenium phthalocyanine complexes with donor substituents
Electron-rich ruthenium phthalocyanine complexes were evaluated in carbene transfer reactions from ethyl diazoacetate (EDA) to aromatic and aliphatic olefins as well as to a wide range of aromatic, heterocyclic and aliphatic amines for the first time. It was revealed that the ruthenium octabutoxyphthalocyanine carbonyl complex [(BuO)8Pc]Ru(CO) is the most efficient catalyst converting electron-rich and electron-poor aromatic olefins to cyclopropane derivatives with high yields (typically 80-100%) and high TON (up to 1000) under low catalyst loading and nearly equimolar substrate/EDA ratio. This catalyst shows a rare efficiency in the carbene insertion into amine N-H bonds. Using a 0.05 mol% catalyst loading, a high amine concentration (1 M) and 1.1 eq. of EDA, a number of structurally divergent amines were selectively converted to mono-substituted glycine derivatives with up to quantitative yields and turnover numbers reaching 2000. High selectivity, large substrate scope, low catalyst loading and practical reaction conditions place [(BuO)8Pc]Ru(CO) among the most efficient catalysts for the carbene insertion into amines.
Cailler, Lucie P.,Kroitor, Andrey P.,Martynov, Alexander G.,Gorbunova, Yulia G.,Sorokin, Alexander B.
supporting information
p. 2023 - 2031
(2021/02/26)

Selective Functionalization of Aliphatic Amines via Myoglobin-Catalyzed Carbene N-H Insertion
Engineered myoglobins have recently gained attention for their ability to catalyze a variety of abiological carbene transfer reactions including the functionalization of amines via carbene insertion into N-H bonds. However, the scope of myoglobin and other hemoprotein-based biocatalysts in the context of this transformation has been largely limited to aniline derivatives as the amine substrates and ethyl diazoacetate as the carbene donor reagent. In this report, we describe the development of an engineered myoglobin-based catalyst that is useful for promoting carbene N-H insertion reactions across a broad range of substituted benzylamines and α-diazo acetates with high efficiency (82-99percent conversion), elevated catalytic turnovers (up to 7,000), and excellent chemoselectivity for the desired single insertion product (up to 99percent). The scope of this transformation could be extended to cyclic aliphatic amines. These studies expand the biocatalytic toolbox available for the selective formation of C-N bonds, which are ubiquitous in many natural and synthetic bioactive compounds.
Fasan, Rudi,Sreenilayam, Gopeekrishnan,Steck, Viktoria
supporting information
p. 224 - 229
(2020/02/15)

Lithium Amino Alkoxide-Evans Enolate Mixed Aggregates: Aldol Addition with Matched and Mismatched Stereocontrol
Building on structural and mechanistic studies of lithiated enolates derived from acylated oxazolidinones (Evans enolates) and chiral lithiated amino alkoxides, we found that amino alkoxides amplify the enantioselectivity of aldol additions. The pairing of enantiomeric series affords matched and mismatched stereoselectivities. The structures of mixed tetramers showing 2:2 and 3:1 (alkoxide-rich) stoichiometries are determined spectroscopically. Rate and computational studies provide a viable mechanistic and stereochemical model based on the direct reaction of the 3:1 mixed tetramers, but they raise unanswered questions for the 2:2 mixed aggregates.
Jermaks, Janis,Tallmadge, Evan H.,Keresztes, Ivan,Collum, David B.
supporting information
p. 3077 - 3090
(2018/03/08)

Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement
A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of α-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammonium salt generation from the allylic phosphate and the glycine aryl ester. Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea benzotetramisole forms syn-α-amino acid derivatives with high diastereo- and enantioselectivity. This methodology is most effective using 4-nitrophenylglycine esters and tolerates a variety of substituted cinnamic and styrenyl allylic ethyl phosphates. The use of challenging unsymmetrical N-allyl-N-methylglycine esters is also tolerated under the catalytic relay conditions without compromising stereoselectivity.
Spoehrle, Stéphanie S. M.,West, Thomas H.,Taylor, James E.,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information
p. 11895 - 11902
(2017/09/07)

Development of a series of bis-triazoles as G-quadruplex ligands
Maintenance of telomeres-specialized complexes that protect the ends of chromosomes-is provided by the enzyme complex telomerase, which is a key factor that is activated in more than 80% of cancer cells, but absent in most normal cells. Targeting telomere maintenance mechanisms could potentially halt tumour growth across a broad spectrum of cancer types. Telomeric ends of chromosomes consist of noncoding repeat sequences of guanine-rich DNA. These G-rich ends can fold into structures called G-quadruplexes. Stabilization of G-quadruplexes by small binding molecules called G4 ligands can prevent telomerase enzyme from maintaining telomere integrity in cancer cells. G-quadruplexes can exist in other parts of the genome too, especially within promoter sequences of oncogenes, and also be interesting drug targets. Here, we describe the development of a new series of novel bis-triazoles, designed to stabilize G-quadruplex structures selectively as G4 ligands. FRET assays showed two compounds to be moderately effective G4 binders, with particular affinity for the quadruplex formed by the Hsp90a promoter sequence, and good selectivity for G-quadruplex DNA vs. duplex DNA. However, CD spectroscopy failed to provide any information about the folding topology of the human telomeric G-quadruplex resulting from its interaction with one of the ligands. All the new ligands showed potent cell growth inhibitory properties against human colon and pancreatic cancer cell lines, as evidenced by the MTT assay; notably, they were more potent against cancer cells than in fetal lung fibroblasts. Docking studies were performed to rationalize the affinity of these ligands for binding to the telomeric parallel G-quadruplex DNA.
Saleh, Maysaa M.,Laughton, Charles A.,Bradshaw, Tracey D.,Moody, Christopher J.
p. 47297 - 47308
(2017/10/19)

Unexpected formation of a μ-carbido diruthenium(IV) complex during the metalation of phthalocyanine with Ru3(CO)12 and its catalytic actIVity in carbene transfer reactions
A μ-carbido diruthenium(iv) phthalocyanine complex was prepared for the first time from the free-base octabutoxyphthalocyanine by direct metalation with Ru3(CO)12. The first examples of the catalytic activity of Ru(iv) binuclear phthalocyanines were demonstrated by the cyclopropanation of aromatic olefins and carbene insertion into the N-H bonds of aromatic or aliphatic amines with turnover numbers of 680-1000 and 580-1000, respectively.
Kroitor, Andrey P.,Cailler, Lucie P.,Martynov, Alexander G.,Gorbunova, Yulia G.,Tsivadze, Aslan Yu.,Sorokin, Alexander B.
supporting information
p. 15651 - 15655
(2017/12/02)

NH insertion reactions catalyzed by reusable water-soluble ruthenium(II)-hm-phenyloxazoline complex
A water-soluble Ru(II)-hm-pheox complex was efficiently catalyzed NH insertion of EDA with a broad class of amine derivatives in water/ether biphasic medium to deliver the biologically active precursors α-aminoester products with excellent yields (up to >99%). The products were separated by decantation and the catalyst was washed and reused several times (at least 8 times) without any specific loss of its catalytic activity. The plausible mechanism of the reaction was explained. Additionally, In case of ethylene diamine, the NH insertion product could be transformed to biological active piperazinone compound in high yield. The asymmetric version of this catalytic reaction is under investigation.
Abu-Elfotoh, Abdel-Moneim
supporting information
p. 4750 - 4754
(2017/11/29)

COMPOUNDS USEFUL AS CSF1 MODULATORS
This invention relates to novel compounds and to pharmaceutical compositions comprising the novel compounds. More specifically, the invention relates to compounds useful as Colony Stimulating Factor 1 Receptor (cFMS) modulators (e.g. cFMS inhibitors). This invention also relates to processes for preparing the compounds, uses of the compounds in treatment and methods of treatment employing the compounds. Specifically, the invention relates to the use of the compounds for the treatment of cancer and autoimmune diseases.
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Paragraph 00299; 00300; 00301

(2016/04/26)

Synthesis of a Gemcitabine Prodrug for Remote Loading into Liposomes and Improved Therapeutic Effect
The chemotherapeutic gemcitabine was actively and stably loaded into lipid nanoparticles through the formation of a prodrug. Gemcitabine was chemically modified to increase the lipophilicity and introduce a weak base moiety for remote loading. Several derivatives were synthesized and screened for their potential to be good liposomal drug candidates for remote loading by studying their solubility, stability, cytotoxicity, and loading efficiency. Two morpholino derivatives of GEM (22 and 23) were chosen as the preferred prodrugs for this purpose as they possessed the best loading efficiencies (100% for drug-to-lipid ratio of 0.36 w/w). This is a considerable improvement over a passive loading strategy where typical loading efficiencies are on the order of ～10-20% for a drug-to-lipid ratio of ～0.01. Liposomes loaded with these two prodrugs were studied in an s.c. tumor model in vivo and showed improved therapeutic effect over free GEM (～2-fold) and saline control (8- to 10-fold). This work demonstrates how chemical modification of a known hydrophilic drug can lead to improved loading, stability, and drug delivery in vivo.
May, Jonathan P.,Undzys, Elijus,Roy, Aniruddha,Li, Shyh-Dar
p. 226 - 237
(2016/02/05)

MYOGLOBIN-BASED CATALYSTS FOR CARBENE TRANSFER REACTIONS
Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).
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Paragraph 0074; 00271

(2016/06/14)

PROTEIN KINASE INHIBITORS
A compound of formula (I), wherein R3, R4, G, B, M, and Z are as defined in the claims, and pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as FGFR inhibitors and are useful in the treatment of a condition, where FGFR kinase inhibition is desired, such as cancer.
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Paragraph 0162

(2015/02/18)

1,8-Naphthyridines IX. Potent anti-inflammatory and/or analgesic activity of a new group of substituted 5-amino[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6- carboxamides, of some their Mannich base derivatives and of one novel substituted 5-amino-10-oxo-10H-pyrimido[1,2-a][1,8]naphthyridine-6-carboxamide derivative
A new group of 5-(alkylamino)-9-isopropyl[1,2,4]triazolo[4,3-a][1,8] naphthyridine derivatives bearing a CONHR group at the 6-position (1c-g), designed to obtain new effective analgesic and/or anti-inflammatory agents, were synthesized and tested along with three new 9-alkyl-5-(4-alkyl-1-piperazinyl)- N,N-diethyl [1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides (2b-d). Besides, a new class of analogues of compounds 1 and 2, bearing a Mannich base moiety at the 9-position (12a-d), as well as the novel N,N-diethyl-5- (isobutylamino)-8-methyl-10-oxo-10H-pyrimido[1,2-a][1,8]naphthyridine-6- carboxamide (15) were prepared and tested. Compounds 1c-g exhibited very interesting anti-inflammatory properties in rats, whereas compounds 2b-d and 15 proved to be endowed with prevalent analgesic activity frequently associated with sedative effects in mice. On the contrary, the Mannich bases 12a-d resulted inactive. The most effective (80% inhibition of oedema) and potent (threshold dose 1.6 mg kg-1 with 31% inhibition of oedema) anti-inflammatory compound 1d did not show gastrolesive effects following 100 mg kg-1 oral administration in rats.
Di Braccio, Mario,Grossi, Giancarlo,Alfei, Silvana,Ballabeni, Vigilio,Tognolini, Massimiliano,Flammini, Lisa,Giorgio, Carmine,Bertoni, Simona,Barocelli, Elisabetta
p. 394 - 405
(2014/10/15)

Selective α-amination and α-acylation of esters and amides via dual reactivity of O-acylhydroxylamines toward zinc enolates
Selective α-amination and α-acylation of esters and amides have been developed, employing O-acylhydroxylamines as a dually reactive aminating and acylating reagent. Treatment of zinc enolates with O-acylhydroxylamines provides solely 1,3-dicarbonyl compounds under mild conditions. Introduction of a copper catalyst into the system shifts the reactivity entirely, yielding α-amination products exclusively.
McDonald, Stacey L.,Wang, Qiu
supporting information
p. 2535 - 2538
(2014/03/21)

PROTEIN KINASE INHIBITORS
A compound of formula (I), wherein R3, R4, G, B, M, and Z are as defined in the claims, and pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as FGFR inhibitors and are useful in the treatment of a condition, where FGFR kinase inhibition is desired, such as cancer.
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Page/Page column 44

(2013/04/25)

Design, synthesis and anti-itch activity evaluation of aromatic amino acid derivatives as gastrin-releasing peptide receptor antagonists
Eight aromatic amino acid derivatives (9a-9h) as gastrin-releasing peptide receptor (GRPR) antagonists were designed and synthesized. For the design, the tertiary structure of GRPR was predicted by blast searching in the premise of 1u19 protein as the template. Eight target compounds were docked into the binding pocket to investigate their possible binding interactions. Their anti-itch activities were tested by intrathecal injection using Kunming mice as experimental animals and chloroquine phosphate as a modeling medium. Compounds 9e and 9f significantly inhibited scratching behaviors. The anti-itch activities of these compounds decreased with the following sequence: 9e > 9f = 9d > 9b > 9g > 9a > 9h > 9c predicted by computer-aided drug design (CADD) and 9e > 9f > 9b > 9h > 9g > 9d > 9a > 9c evaluated by preliminary test. They were broadly in line with activity order pretested by CADD. It showed that the predicted tertiary structure of GRPR could be used for antipruritic drug design.
Yao, Ri-Sheng,Li, Ting-Ting,Xu, Jun,Jiang, Lai-En,Ruan, Ban-Feng
p. 865 - 873
(2012/10/29)

Synthesis of carbamoylacetates from α-iodoacetate, CO, and amines under Pd/light combined conditions
We developed a novel synthetic method of carbamoylacetates from -iodoacetate, carbon monoxide, and amines under photoirradiation conditions in the presence of a Pd catalyst. This reaction likely proceeds via interplay of radical and organopalladium species. Georg Thieme Verlag Stuttgart · New York.
Sumino, Shuhei,Fusano, Akira,Fukuyama, Takahide,Ryu, Ilhyong
experimental part
p. 1331 - 1334
(2012/07/13)

New potentially dhelating chiral magnesium amide bases for use in enantioselective deprotonation reactions
A series of chiral secondary amines, incorporating a five- or six-membered heterocycle, were synthesised and used to prepare novel chiral magnesium bisamide reagents. These amide bases were subsequently applied within asymmetric deprotonation reactions to
Kerr, William J.,Middleditch, Michael,Watson, Allan J. B.
supporting information; experimental part
p. 177 - 180
(2011/03/22)

Ruthenium Catalysts and Uses Thereof
Ruthenium nanoparticles supported on non-cross-linked soluble polystyrene were prepared by reacting [RuCl2(C6H5CO2Et)]2 with polystyrene in open air. They effectively catalyze intra- and intermolecular carbenoid insertion into C—H and N—H bonds, alkene cyclopropanation, and ammonium ylide/[2,3]-sigmatropic rearrangement reactions. This supported ruthenium catalyst is much more reactive than [RuCl2(p-cymene)]2 and Ru(Por)CO] for catalytic intermolecular carbenoid C—H bond insertion into saturated alkanes. By using a-diazoacetamide as a substrate for intramolecular carbenoid C—H insertion, the supported ruthenium catalyst can be to recovered and reused for ten successive iterations without significant loss of activity.
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Page/Page column 4; 9

(2011/02/15)

MAXI-K CHANNEL BLOCKERS AND METHODS OF USE
This invention relates to the use of potent potassium channel blockers or a formulation thereof in the treatment of glaucoma and other conditions which leads to elevated intraocular pressure in the eye of a patient. This invention also relates to the use of such compounds to provide a neuroprotective effect to the eye of mammalian species, particularly humans.
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Page/Page column 70

(2009/05/28)

Triton B-mediated mild, convenient, and efficient method for the selective alkylation of cyclic secondary amines and thiols
Alkylation of cyclic secondary amines, thiols, and pyridazinones has been demonstrated with alkyl halides using Triton B as base and reaction medium.
Meshram,Reddy, B. Chennakesava,Goud, P. Ramesh
experimental part
p. 2297 - 2303
(2009/12/01)

Leishmanicidal potential of N-substituted morpholine derivatives: Synthesis and structure-activity relationships
A series of N-substituted morpholines 2-20 was synthesised by reacting various acid chlorides and alkyl halides with morpholine (1). All of the synthesised compounds 2-20 were screened for their leishmanicidal effects using amphotericin B (IC50 = 0.24 μg L-1) and pentamidine (IC50 = 2.56 μg mL-1) as standards and a structure-activity relationship (SAR) study was established. The compounds 2 (IC50 = 48 μg mL-1), 3 (IC50 = 30.0 μg mL-1), 10 (IC50 = 41.0 μg mL-1), 15 (IC50 = 33.0 μg mL-1), 16 (IC50 = 35.0 μg mL-1) and 20 (IC50 = 47.0 μg mL-1) showed weak leishmanicidal activities.
Khan, Khalid Mohammed,Khan, Muhammad Zarrar,Taha, Muhammad,Maharvi, Ghulam Murtaza,Saify, Zafar Saeed,Parveen, Shahnaz,Choudhary, Muhammad Iqbal
experimental part
p. 479 - 484
(2010/06/21)

Nanocrystalline copper(II) oxide catalyzed aza-Michael reaction and insertion of α-diazo compounds into N-H bonds of amines
Nanocrystalline copper(II) oxide efficiently catalyzed the conjugate addition of aliphatic amines to α,β-unsaturated compounds to produce β-amino compounds with excellent yields under mild reaction conditions. Similarly, Glycine esters are obtained in good yields by the insertion of α-diazoacetate into N-H bonds of amines. The catalyst is used for three cycles with minimal loss of activity.
Kantam, M. Lakshmi,Laha, Soumi,Yadav, Jagjit,Jha, Shailendra
experimental part
p. 4467 - 4469
(2009/12/01)

Iron(III) corroles and porphyrins as superior catalysts for the reactions of diazoacetates with nitrogen- or sulfur-containing nucleophilic substrates: Synthetic uses and mechanistic insights
A thorough mechanistic investigation has been performed on the reactions of primary and secondary amines with diazoacetates, which proceed uniquely quickly and efficiently when catalyzed by iron(III) corroles and porphyrins. Two major differences in relation to other metal-based catalysts are that the iron complexes are not poisoned by excess amine and that metal-carbene intermediates are apparently not involved in the reaction pathway. The results instead point towards nitrogen ylide intermediates formed by nucleophilic attack of the amines on diazoacetate-coordinated iron complexes. Nitrogen ylides are also formed when allyl- and propargylsubstituted tertiary amines react with diazoacetates, a scenario that smoothly leads to 2,3-rearrangement reaction products with catalytic amounts of the iron(III) complexes. Similar findings regarding the superiority of the iron-(III) complexes (in terms of catalyst loading, chemical yields, and reaction conditions) were obtained with thiols (S-H insertion) and sulfides (2,3-rear-rangement reactions), which suggest similar mechanisms operate in these cases.
Aviv, Iris,Gross, Zeev
scheme or table
p. 3995 - 4005
(2009/05/26)

Ruthenium(III) chloride-catalyzed efficient protocol for ethyl diazoacetate insertion into the N-H bond of secondary amines
Ruthenium(III) chloride (1 mol%) alone can catalyze the insertion of ethyl diazoacetate into N-H bonds of various structurally and electronically diverse secondary cyclic amines under solvent-free conditions to afford the corresponding glycine esters in g
Varala, Ravi,Enugala, Ramu,Adapa, Srinivas R.
experimental part
p. 1369 - 1372
(2009/12/04)

4-AMINO-2,6-DIMETHYLPHENOL COMPOUND, PROCESS FOR ITS PREPARATION AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
A 4-amino-2, 6-dimethylphenol compound having the formula given in the description, acid-addition salts thereof, a process for preparing them, pharmaceutical composition comprising them and its use as anti-pyretic and anti-nociceptive agents.
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Page/Page column 5-6

(2008/06/13)

Iron corroles and porphyrins as very efficient and highly selective catalysts for the reactions of α-diazo esters with amines
Iron corroles and porphyrins catalyze the reactions of amines with ethyl diazoacetate extremely efficiently, leading to complete and rapid conversion into N-substituted glycine ethyl esters by simultaneous addition of the substrates to the catalysts. The selectivity toward activation of the NH bonds is remarkable and quite different from other catalysts. Georg Thieme Verlag Stuttgart.
Aviv, Iris,Gross, Zeev
p. 951 - 953
(2007/10/03)

METHODS AND COMPOUNDS FOR INHIBITING MRP1
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(2008/06/13)

Pyrimidine derivatives and processes for the preparation thereof
The present invention relates to novel pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts thereof which possess an excellent anti-secretory activity, pharmaceutical compositions containing the same as an active ingredient, their novel intermediates, and processes for the preparation thereof wherein: when A is piperidin-1-yl or —NH—B, wherein B is C3-C4alkyl, C3-C4alkenyl, C3-C7cycloalkyl, C1-C3alkoxyethyl, phenylethl which may be substituted or unsubstituted, 3-trifluoromethylphenylmethyl, 1-naphthylmethyl, 4-methylthiazol-2-yl or 4-phenylthiazol-2-yl, R1is hydrogen or methyl; and R2, R3, R4and R5are hydrogen; or when A is a group of formula (II); when R1is hydroxymethyl or C1-C3alkoxymethyl, R2, R3, R4, R5and R6are hydrogen; and R7is hydrogen or halogen; or when R1is hydrogen or methyl, R7is hydrogen or halogen; and one or two of R2, R3, R4, R5and R6is hydroxy, methoxy, or a group of formula (III) wherein Z is C1-C4alkyl, substituted or unsubstituted C1-C4alkenyl, cyloalkyl, benzyloxyalkyl, alkoxycarbonylalkyl, morpholinomethyl, piperidinomethyl, 4-substituted-piperazinomethyl, substituted or unsubstituted phenyl, naphthyl, substituted or unsubstituted benzyl, thiophen-2-yl-methyl, 1-substituted-pyrrolidin-2-yl or —CHR8NHR9, wherein R8is hydrogen, methyl, isopropyl, benzyl, benzyloxymethyl, methylthioethyl, benzyloxycarbonylmethyl, carbamolymethyl, carbamoylethyl, or 1-benzylimidazol-4-ylmethyl and R9is hydrogen or t-butoxycarbonyl; and the others are hydrogen or methyl.
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Page column 13

(2008/06/13)

Catalytic insertion of diazo compounds into N-H bonds: The copper alternative
The complexes TpXCu (TpX = homoscorpionate) catalyse the insertion of diazo compounds into nitrogen-hydrogen bonds of amines and amides, under very mild conditions, with quantitative yields being obtained with equimolar ratios of reactants.
Morilla, M. Esther,Diaz-Requejo, M. Mar,Belderrain, Tomas R.,Nicasio, M. Carmen,Trofimenko, Swiatoslaw,Perez, Pedro J.
p. 2998 - 2999
(2007/10/03)

Design of a new cascade reaction for the construction of complex acyclic architecture: The tandem acyl-claisen rearrangement
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Dong,Macmillan
p. 2448 - 2449
(2007/10/03)

13C CP MAS NMR, FTIR, X-ray diffraction and PM3 studies of some N-(ω-carboxyalkyl)morpholine hydrohalides
N-(ω-carboxyalkyl)morpholine hydrochlorides, OC4H8N(CH2)nCOOH·HCI, n = 1-5, were obtained and analyzed by 13C cross polarization (CP) magic angle spinning (MAS) NMR, FTIR and PM3 calculations. The structure of N-(3-carboxy-propyl)morpholine hydrochloride (n = 3) has been solved by X-ray diffraction method at 100 K and refined to the R = 0.031. The crystals are monoclinic, space group P21/c, a = 14.307(3), b = 9.879(2), c = 7.166(1) A?, β = 93.20(3)°, V = 1011.3(3) A?3, Z = 4. In this compound the nitrogen atom is protonated and two molecules form a centrosymmetric dimer, connected by two N+-H···Cl- (3.095(1) A?) and two O-H···Cl- (3.003(1) A?) hydrogen bonds. 13C CP MAS NMR spectra, contrary to the solution, showed non-equivalence of the ring carbon atoms. The PM3 calculations predict a molecular dimer without proton transfer for an HCl complex, while for an HBr complex an ion pairs with proton transfer, and reproduces correctly the conformation of both dimers but overestimates H-bond distances. Shielding constants calculated from the PM3 geometry of ion pairs gave a linear correlation with the 13C chemical shifts in solids.
Dega-Szafran,Ga?szczyk,Maciejewska,Szafran,Tykarska,Wawer
p. 261 - 273
(2007/10/03)

Synthesis and in vitro evaluation of novel morpholinyl- and methylpiperazinylacyloxyalkyl prodrugs of 2-(6-methoxy,2-naphthyl)propionic acid (naproxen) for topical drug delivery
Various novel morpholinyl- (3a,b) and methylpiperazinylacyloxyalkyl (3c- f) esters of 2-(6-methoxy-2-naphthyl)propionic acid were synthesized and evaluated in vitro for topical drug delivery as potential prodrugs of naproxen (1). Compounds 3a-f were prepared by coupling the corresponding naproxen hydroxyalkyl ester with the morpholinyl- or (4-methyl-1- piperazinyl)acyl acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)-pyridine (DMAP) and quantitatively hydrolyzed (t(1/2) = 1- 26 min) to naproxen in human serum. Compounds 3c-f showed higher aqueous solubility and similar lipophilicity, determined by their octanol-buffer partition coefficients (log P(app)), at pH 5.0 when compared to naproxen. At pH 7.4 they were significantly more lipophilic than naproxen. The best prodrug 3c led to a 4-and 1.5-fold enhancement of skin permeation when compared to naproxen at pH 7.4 and 5.0, respectively. The present study indicates using a methylpiperazinyl group yields prodrugs that are partially un-ionized under neutral and slightly acidic conditions, and thus, a desirable combination is achieved in terms of aqueous solubility and lipophilicity. Moreover, the resulting combination of biphasic solubility and fast enzymatic hydrolysis of the methylpiperazinylacyloxyalkyl derivatives gave improved topical delivery of naproxen.
Rautio, Jarkko,Nevalainen, Tapio,Taipale, Hannu,Veps?l?inen, Jouko,Gynther, Jukka,Laine, Krista,J?rvinen, Tomi
p. 1489 - 1494
(2007/10/03)

Syntheses des alkyl-1 cyclanols fonctionnalises aux positions α, β et γ de la chaine hydrocarbonee
We have developed a general and versatile synthesis of N,N-dialkylaminoalkyl-, 1-chloroalkyl-, 1-phenoxyalkyl-, 1-thiophenoxyalkyl-, 1-diethoxyalkyl-, and 1-(1,3-dithiolane)alkylcyclanols in good yields by the reaction of α,ω-bis(bromomagnesio)alkanes with the corresponding functionalized carboxylic acid esters.
Canonne, P.,Belley, M.,Fytas, G.,Plamondon, J.
p. 168 - 173
(2007/10/02)

NOVEL PALLADIUM COMPLEX-CATALYZED REACTION OF MAGNESIUM AMIDES WITH ALLYLIC ELECTROPHILES
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Dzhemilev, U. M.,Ibragimov, A. G.,Minsker, D. L.,Muslukhov, R. R.
p. 365 - 368
(2007/10/02)