- Environmentally benign process for the synthesis of N-formyl amino acid esters
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Several amino acid ester hydrochlorides were reacted with ammonium formate to give N-formyl amino acid esters in good yields.
- Kotha, Sambasivarao,Behera, Manoranjan,Khedkar, Priti
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Read Online
- Isocyanide-Induced Esterification of Sulfinic Acids to Access Sulfinates
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The isocyanide-induced esterification of sulfinic acids with alcohols or thiophenols access to sulfinates has been developed. Various primary, secondary, and tertiary alcohols could be compatible with the established protocols. Notably, such an isocyanide-induced synthetic strategy presented the advantages of simple operation, good functional group tolerance, and more than 40 examples up to 99% yields. (Figure presented.).
- Yang, Jianjing,Dong, Haozhe,Yan, Kelu,Song, Xiaodan,Yu, Jie,Wen, Jiangwei
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supporting information
p. 5417 - 5421
(2021/09/29)
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- Dispirooxindoles based on 2-selenoxo-imidazolidin-4-ones: Synthesis, cytotoxicity and ros generation ability
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A regio-and diastereoselective synthesis of two types of dispiro derivatives of 2-selenoxoim-idazolidin-4-ones, differing in the position of the nitrogen atom in the central pyrrolidine ring of the spiro-fused system—namely, 2-selenoxodispiro[imidazolidine-4,3′-pyrrolidine-2′,3′′-indoline]-2′′, 5-diones (5a-h) and 2-senenoxodispiro[imidazolidine-4,3′-pyrrolidine-4′,3′′-indoline]-2′′,5-diones (6a-m)—were developed based on a 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or formaldehyde and sarcosine to 5-arylidene or 5-indolidene-2-selenoxo-tetrahydro-4H-imidazole-4-ones. Selenium-containing dispiro indolinones generally exhibit cytotoxic activity near to the activity of the corresponding oxygen and sulfur-containing derivatives. Compounds 5b, 5c, and 5e demonstrated considerable in vitro cytotoxicity in the 3-(4,5-dimethylthiazol-2-yl)2,5-diphenyl tetrazolium bromide (MTT) test (concentration of compounds that caused 50% death of cells (CC50) 7.6–8.7 μM) against the A549 cancer cell line with the VA13/A549 selectivity index 5.2– 6.9 and compound 6e—against the MCF7 cancer cell line (CC50 20.6 μM, HEK293T/A549 selectivity index 1.6); some compounds (5 and 6) increased the level of intracellular reactive oxygen species (ROS) in the experiment on A549 and PC3 cells using platinized carbon nanoelectrode. The tests for p53 activation for compounds 5 and 6 on the transcriptional reporter suggest that the investigated compounds can only have an indirect p53-dependent mechanism of action. For the compounds 5b, 6b, and 6l, the ROS generation may be one of the significant mechanisms of their cytotoxic action.
- Novotortsev, Vladimir K.,Kukushkin, Maxim E.,Tafeenko, Viktor A.,Skvortsov, Dmitry A.,Kalinina, Marina A.,Timoshenko, Roman V.,Chmelyuk, Nelly S.,Vasilyeva, Liliya A.,Tarasevich, Boris N.,Gorelkin, Petr V.,Erofeev, Alexander S.,Majouga, Alexander G.,Zyk, Nikolai V.,Beloglazkina, Elena K.
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- ANTIVIRAL 1,3-DI-OXO-INDENE COMPOUNDS
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The invention provides compounds of Formula (I): as described herein, along with pharmaceutically acceptable salts, pharmaceutical compositions containing such compounds, and methods to use these compounds, salts and compositions for treating viral infections.
- -
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Paragraph 0297
(2021/10/22)
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- Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas
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Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.
- Yang, Zheng-Lin,Xu, Xin-Liang,Chen, Xue-Rong,Mao, Zhi-Feng,Zhou, Yi-Feng
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supporting information
p. 648 - 652
(2020/12/21)
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- Influence of the C-terminal substituent on the crystal-state conformation of Adm peptides
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The bis-functionalized diamondoid α-amino acid 2-aminoadamantane-2-carboxylic acid (Adm) has been used as the building block of four Nα-formyl homo-dipeptide alkylamide sequences via a solution-phase Ugi multicomponent reaction approach. The conformers of these peptides have been determined in the crystalline state by X-ray diffraction to distinguish the influences of the C-terminal substituent. One of the Adm peptides folds into an open and a hydrogen-bonded γ-turn geometry. Moreover, 3D-structures have been observed featuring two consecutive γ-turns in an incipient γ-helical structure, a significantly distorted nonhelical β-turn, as well as an S-shaped conformation with opposite helical screw senses. A significant topological variety is thus exhibited by the -Adm-Adm- sequences contingent on their C-terminal substituents, illustrating both the broad conformational potential and the need for further characterization of this sterically bulky residue in explorations of its ?, ψ space.
- Mir, Fatemeh M.,Crisma, Marco,Toniolo, Claudio,Lubell, William D.
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- Facile access to: N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones
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N-Formamide synthesis using N-formyl imide with primary and secondary amines with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH·H2O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines with TsOH·H2O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole and quinazolinone derivatives. Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- A nd metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation.
- Huang, Hsin-Yi,Liang, Chien-Fu,Lin, Xiu-Yi,Yen, Shih-Yao
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supporting information
p. 5726 - 5733
(2020/08/21)
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- One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction
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A pseudo-five-multicomponent reaction involving an isocyanide, a primary amine, two molecules of formaldehyde and water is reported, which gives N,N′-substituted 4-imidazolidinones when trifluoroethanol is used as the solvent. The reaction proceeds with good yields and with a wide variety of amines and isocyanides, providing an efficient new entry to these heterocycles. A preliminary study of the reaction mechanism suggests that trifluoroethanol, although acting as the solvent, is directly involved as a reagent in the reaction pathway.
- Attorresi, Cecilia I.,Bonifazi, Evelyn L.,Ramírez, Javier A.,Gola, Gabriel F.
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supporting information
p. 8944 - 8949
(2018/12/10)
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- PROCESSES FOR THE PREPARATION OF DIASTEREOMERICALLY AND ENANTIOMERICALLY ENRICHED OXAZOLINES
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The invention relates to an industrially viable and advantageous process for the preparation of (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid, having the following formula (I) generally known as Droxidopa, or of intermediates useful in the synthesis thereof.
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Page/Page column 22-23
(2017/05/28)
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- Tetraethylorthosilicate as a mild dehydrating reagent for the synthesis of N-formamides with formic acid
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The synthesis of N-formamides with formic acid as a formyl source under mild conditions was achieved using tetraethylorthosilicate (TEOS), a low cost and environmentally benign reagent. The mild conditions in this system enable the formylation of a variety of amino acid derivatives including stereochemically labile phenylglycine ethyl ester with 96% ee. This new protocol could also be applied to simple amines including weakly basic aniline derivatives, giving various primary and secondary formamides.
- Nishikawa, Yasuhiro,Nakamura, Hidetsugu,Ukai, Norimitsu,Adachi, Wakana,Hara, Osamu
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supporting information
p. 860 - 863
(2017/02/10)
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- A copper-catalyzed formal O-H insertion reaction of α-diazo-1,3- dicarbonyl compounds to carboxylic acids with the assistance of isocyanide
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A novel copper-catalyzed formal O-H insertion of α-diazo-1,3- dicarbonyl compounds to carboxylic acids has been developed, providing a straightforward synthetic method for α-acyloxy-1,3-dicarbonyl compounds, in which the activation of carboxylic acids by isocyanide plays a crucial role.
- Wang, Zikun,Bi, Xihe,Liang, Yongjiu,Liao, Peiqiu,Dong, Dewen
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p. 3976 - 3978
(2014/04/03)
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- PEPTIDE EPOXYKETONE COMPOUNDS
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The present disclosure relates to novel compounds and pharmaceutical compositions thereof which are useful as inhibitors of proteasomes. The compounds provided herein are capable of inhibiting all three of CT-L, T-L, and PGPH activities of proteasomes, and are useful in treating various conditions or diseases associated with proteasomes.
- -
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Paragraph 00299; 00300
(2014/02/16)
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- PYRROLOPYRIDAZINE JAK3 INHIBITORS AND THEIR USE FOR THE TREATMENT OF INFLAMMATORY AND AUTOIMMUNE DISEASES
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Disclosed are compounds of formula (I) and pharmaceutically acceptable salts thereof. The compounds of formula (I) inhibit tyrosine kinase activity of JAK3, thereby making them useful for the treatment of inflammatory and autoimmune diseases.
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Page/Page column 67-68
(2012/10/07)
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- PYRROLOPYRIDAZINE JAK3 INHIBITORS AND THEIR USE FOR THE TREATMENT OF INFLAMMATORY AND AUTOIMMUNE DISEASES
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Disclosed are compounds of Formula (I), and pharmaceutically acceptable salts thereof. The compounds of formula (I) inhibit tyrosine kinase activity of JAK3, thereby making them useful for the treatment of inflammatory and autoimmune diseases.
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Page/Page column 78
(2012/10/07)
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- Studies toward novel peptidomimetic inhibitors of thioredoxin-thioredoxin reductase system
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Thioredoxins (Trx) are ubiquitous multifunctional low-molecular weight proteins that together with thioredoxin reductases (TrxR) participate in the maintenance of protein thiol homeostasis in NADPH-dependent reactions. An increasing number of data reveal that the Trx-TrxR system is an attractive target for anticancer therapies. In this work, we have elaborated a new and simple synthetic approach employing Ugi reaction to synthesize several new inhibitors of this system. The influence of various electrophilic fragments of this new class of compounds on the inhibition of the Trx-TrxR system was evaluated. As a result, a new compound 19a (SK053), which inhibits the activity of the Trx-TrxR system and exhibits antitumor activity, was obtained. Biologic analyses revealed that 19a inhibits induction of NF-κB and AP-1 and decreases H2O2 scavenging capacity in tumor cells. Altogether, we show that 19a is a novel potential antitumor peptidomimetic inhibitor that can be used as a starting compound for further optimization.
- K?ossowski, Szymon,Muchowicz, Angelika,Firczuk, Ma?gorzata,?wiech, Marta,Redzej, Adam,Golab, Jakub,Ostaszewski, Ryszard
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scheme or table
p. 55 - 67
(2012/02/15)
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- A remarkably simple protocol for the N -formylation of amino acid esters and primary amines
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A simple, convenient, and wide scope protocol for the N-formylation of amino acid esters and primary amines has been developed utilizing only imidazole in warm DMF.
- Suchy, Mojmir,Elmehriki, Adam A. H.,Hudson, Robert H. E.
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supporting information; experimental part
p. 3952 - 3955
(2011/09/19)
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- NOVEL FUSED PYRIDAZINE DERIVATIVES
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The present invention relates to novel fused pyridazine compounds, their pharmaceutically acceptable salts, and their isomers, stereoisomers, conformers, tautomers, polymorphs, hydrates and solvates. The present invention also encompasses pharmaceutically acceptable compositions of said compounds and process for preparing novel compounds. The invention further relates to the use of the above-mentioned compounds for the preparation of medicament for use as pharmaceuticals.
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Page/Page column 73-74
(2011/05/06)
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- Leccinine A, an endoplasmic reticulum stress-suppressive compound from the edible mushroom Leccinum extremiorientale
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Leccinine A (1) along with a known compound (2), were isolated from the edible mushroom Leccinum extremiorientale. The structure of 1 was determined by the interpretation of spectral data. Leccinine A showed protective activity against endoplasmic reticulum stress-dependent cell death. Seven analogues (3-9) of 1 were synthesized in order to evaluate the structure-activity relationship, and the result indicated that the formamide group of 1 was indispensable for the activity.
- Choi, Jae-Hoon,Ozawa, Nobuhiko,Yamakawa, Yasuhiro,Nagai, Kaoru,Hirai, Hirofumi,Kawagishi, Hirokazu
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experimental part
p. 6649 - 6653
(2011/09/30)
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- Isoselenocyanates derived from amino acid esters: An expedient synthesis and application to the assembly of selenoureidopeptidomimetics, unsymmetrical Selenoureas and selenohydantoins
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An important class of organoselenium compounds-α-isoselenocyanato esters 4 hasbeen prepared by a reaction of α-isocyano esters with elemental selenium powder. The reaction issimple, rapid and all the isoselenocyanates havebeen isolated as stable ones after chromatographic purification. These hitherto unreported classes of molecules would be useful building blocks for the preparation of variety of selenium containing peptidomimetics. In this study, the utility of the title molecules in the preparation of selenoureidopeptidomimetics 6, unsymmetrical selenoureas 8 and selenohydantoins 10 isdemonstrated.
- Hemantha, Hosahalli P.,Sureshbabu, Vommina V.
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scheme or table
p. 644 - 651
(2011/09/14)
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- Meso-unsubstituted iron corrole in hemoproteins: Remarkable differences in effects on peroxidase activities between myoglobin and horseradish peroxidase
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(Figure Presented) Myoglobin (Mb) and horseradish peroxidase (HRP) were both reconstituted with a meso-unsubstituted iron corrole and their electronic configurations and peroxidase activities were investigated. The appearance of the 540 nm band upon incorporation of the iron corrole into apoMb indicates axial coordination by the proximal histidine imidazole in the Mb heme pocket. Based on 1H NMR measurements using the Evans method, the total magnetic susceptibility of the iron corrole reconstituted Mb was evaluated to be S = 3/2. In contrast, although a band does not appear in the vicinity of 540 nm during reconstitution of the iron corrole into the matrix of HRP, a spectrum similar to that of the iron corrole reconstituted Mb is observed upon the addition of dithionite. This observation suggests that the oxidation state of the corrole iron in the reconstituted HRP can be assigned as +4. The catalytic activities of both proteins toward guaiacol oxidation are quite different; the iron corrole reconstituted HRP decelerates H2O2-dependent oxidation of guaiacol, while the same reaction catalyzed by iron corrole reconstituted Mb has the opposite effect and accelerates the reaction. This finding can be attributed to the difference in the oxidation states of the corrole iron when these proteins are in the resting state.
- Matsuo, Takashi,Hayashi, Akihiro,Abe, Masato,Matsuda, Takaaki,Hisaeda, Yoshio,Hayashi, Takashi
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supporting information; experimental part
p. 15124 - 15125
(2010/01/30)
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- Synthesis of new cyclopropylisonitriles and their applications in Ugi four-component reactions
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Several new cyclopropylisonitriles were synthesized from the corresponding cyclopropylamines (41-69% yield) and utilized in Ugi four-component reactions to furnish 12 new dipeptides in 38-86% yield. The structures of four of these dipeptides were determined by X-ray crystallography. Georg Thieme Verlag Stuttgart.
- Osipova, Anna,Yufit, Dmitrii S.,De Meijere, Armin
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p. 131 - 139
(2008/01/03)
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- A rapid and simple cleanup procedure for metathesis reactions
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Figure presented A new method for easy removal of ruthenium from metathesis reactions by using a polar isocyanide is reported. This protocol removed most ruthenium byproducts from a variety of synthetically useful metatheses. Moreover, the isocyanide-promoted carbene insertion results in rapid destruction of carbene reactivity, demonstrated in the commonly used first- and second-generation Grubbs' carbenes.
- Galan, Brandon R.,Kalbarczyk, Kyle P.,Szczepankiewicz, Steven,Keister, Jerome B.,Diver, Steven T.
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p. 1203 - 1206
(2007/12/30)
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- Process for the production of chiral compounds
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A method for producing chiral compounds according to the condition of a 1.4 Michael reaction, and a compound of formula (31). 1The invention also provides pharmaceutical compositions comprising the compound, and methods for treating pain and other diseases using the pharmaceutical compositions.
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- Pain treatment methods and compositions
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The invention relates to amino acids, a method for the production thereof, medicaments containing said amino acids and the use of amino acids in the production of medicaments for treating pain.
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- Beta-thioamino acids
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Thio-alpha-amino acids of general formula (I), wherein R1, R2 and R3 have the meanings given in the description, methods for producing them, and medicaments containing these compounds. The invention also provides methods for treating pain and other diseases using the pharmaceutical compositions comprising the thioamino acids.
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- Bis(acyloxmethyl)imidazole compounds
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This invention relates to new bis(acyloxymethyl)imidazole derivatives; to compositions comprising these derivatives; and to processes for their utility as fungicides, bactericides and as inhibitors of the growth of cancer, particularly solid tumor cancer, in warm blooded animals of the formula: STR1 wherein M is STR2 or R; each R, R' and R" are independently selected from hydrogen and Z substituted or unsubstituted alkyl, cycloalkyl, cycloalkenyl, alkenyl, aryl, and heterocyclic ring wherein said ring comprises at least one of oxygen, nitrogen, sulfur or silicon; provided that STR3 may form a Z substituted or unsubstituted heterocyclic, and R' and R" attached to the imidazole ring, may form a Z substituted or unsubstituted heterocyclic ring; X is selected from at least one of oxygen, sulfur, nitrogen and alkyl; provided further that silicon is not directly attached to oxygen, sulfur or nitrogen and R' is not hydrogen when X is oxygen or sulfur; and Z is selected from halogen, nitro, nitrile, alkyl, haloalkyl, alkenyl, carboxylic acid, carboxylic acid ester, carboxylic acid amide, ether, thioether, hydroxyl, acylated hydroxyl, sulfonylamide, sulfonylurea, sulfoxide, sulfone, substituted and unsubstituted amine or mixtures thereof.
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- Enol Formates: Ruthenium Catalysed Formation and Formylating Reagents
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The one-step synthesis of the enol formates, isopropenyl, hex-1-en-2-yl, and α-methylenebenzyl formates, directly from terminal alkynes and formic acid with arene-ruthenium(II) catalysts is reported.They have been shown to be effective formylating reagents, under mild and neutral conditions, to produce formamides from primary and secondary amines, formylamino esters, and in the presence of a catalytic amount of imidazole, formates from alcohols or phenols.
- Neveux, Muriel,Bruneau, Christian,Dixneuf, Pierre H.
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p. 1197 - 1199
(2007/10/02)
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- A Convenient Synthesis of Primary Amines Using Sodium Diformylamide as A Modified Gabriel Reagent
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Sodium diformylamide (1) was used as a convenient substitute for phthalimide in the Gabriel synthesis of primary amines.Reagent 1 undergoes smooth N-alkylation with alkyl halides or p-toluenesulfonates 2 in acetonitrile or dimethylformamide to give the corresponding N,N-diformylalkylamines 3 in good yields, except with alkylating agents which are susceptible to base-catalyzed elimination.The formyl group of 3 can be easily removed by hydrochloric acid to give the corresponding alkylamine hydrochlorides 5 or free alkylamines 4.
- Yinglin, Han,Hongwen, Hu
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p. 122 - 124
(2007/10/02)
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- THE SYNTHESIS AND CHEMISTRY OF AZOLENINES. PART 20 ISOLATION OF 3H-PYRROLE-5-CARBOXYLATE ESTERS AND FRAGMENTATION PRODUCTS FROM THE REACTION BETWEEN 2,2-DISUBSTITUTED 1,3-DIKETONES AND GLYCINE ETHYL ESTER HYDROCHLORIDE
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The reaction between 3,3-dimethylpentane-2,4-dione (12a) and glycine ethyl ester hydrochloride (13) in the presence of sodium acetate and acetic acid gives moderate amounts each of ethyl 2,3,3,4-tetramethyl-3H-pyrrole-5-carboxylate (17a), a hydroxypyrroline precursor (15a) and a fragmentation product ethyl acetamidoacetate (14a).With the more sterically-crowded 2,2-dimethyl-1-phenylbutane-1,3-dione (12b), only very small amounts of two regioisomeric 3H-pyrroles (17b) and (18b) are found, fragmentation being the major reaction pathway: other 2,2-disubstituted 1,3-diketones studied gave only fragmentation products.A reaction scheme accounting for the various products is proposed.
- Lee, Sze-Ming,Sammes, Michael P.
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p. 2401 - 2410
(2007/10/02)
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- Design, Synthesis, Antineoplastic Activity, and Chemical Properties of Bis(carbamate) Derivatives of 4,5-Bis(hydroxymethyl)imidazole
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A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia.Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds.However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active.The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia.The solution stability, water solubility, pKa, and log P of carmethizole are also reported.
- Anderson, Wayne K.,Bhattacharjee, Debkumar,Houston, D. Michael
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p. 119 - 127
(2007/10/02)
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