- Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors
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This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound mask
- Sharma, Brijesh M.,Nikam, Arun V.,Lahore, Santosh,Ahn, Gwang-Noh,Kim, Dong-Pyo
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supporting information
(2022/02/25)
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- Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
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Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
- Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
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- Synthesis of α-Amidoketones through the Cascade Reaction of Carboxylic Acids with Vinyl Azides under Catalyst-Free Conditions
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An efficient synthesis of α-amidoketone derivatives through the cascade reactions of carboxylic acids with vinyl azides is presented. Compared with literature protocols, notable features of this new method include catalyst-free conditions, broad substrate scope, good tolerance of a wide range of functional groups, and high efficiency. In addition, the synthetic potential of this method as a tool for late-stage modification was convincingly manifested by its application in the structural elaborations of a number of carboxylic acid drug molecules.
- Gao, Cai,Zhou, Qianting,Yang, Li,Zhang, Xinying,Fan, Xuesen
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p. 13710 - 13720
(2020/11/13)
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- Synthesis method of alpha-acylamino ketone compound
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The invention discloses a synthesis method of an alpha-acylamino ketone compound, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: mixingan alkenyl azide compound 1, a carboxylic acid compound 2 and an organic solvent, and heating to react to obtain the alpha-acylamino ketone compound 3. Compared with the prior art, the method has thefollowing advantages: (1) the synthesis process is simple and efficient, no catalyst is needed in the whole process, and the alpha-acylamino ketone compound can be obtained with high yield by dissolving the alkenyl azide compound and the carboxylic acid compound in the solvent and stirring; (2) raw materials are cheap and easy to obtain, reaction conditions are mild, and operation is simple; (3) the substrate is wide in application range and can be used for modifying drug molecules; and (4) the atom economy is high, and the requirements of green chemistry are met.
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Paragraph 0027-0029; 0030-0032; 0116
(2020/12/08)
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- 1,3-Oxazole-based selective picomolar inhibitors of cytosolic human carbonic anhydrase II alleviate ocular hypertension in rabbits: Potency is supported by X-ray crystallography of two leads
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Two lead 1,3-oxazole-based carbonic anhydrase inhibitors (CAIs) earlier identified as selective, picomolar inhibitors of hCA II (a cytosolic target for treatment of glaucoma) have been investigated further. Firstly, they were found to be conveniently synt
- Ferraroni, Marta,Lucarini, Laura,Masini, Emanuela,Korsakov, Mikhail,Scozzafava, Andrea,Supuran, Claudiu T.,Krasavin, Mikhail
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p. 4560 - 4565
(2017/10/06)
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- Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones
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The esters of 1,2-azido alcohols were transformed into α-amido ketones without external oxidants through the Ru-catalyzed formation of N-H imines with the liberation of N2 followed by intramolecular migration of the acyl moiety. A wide range of α-amido ketones were obtained, and one-pot transformation into the corresponding oxazoles (or a thiazole) was demonstrated.
- Kim, Yongjin,Pak, Han Kyu,Rhee, Young Ho,Park, Jaiwook
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supporting information
p. 6549 - 6552
(2016/06/01)
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- Probing the 'bipolar' nature of the carbonic anhydrase active site: Aromatic sulfonamides containing 1,3-oxazol-5-yl moiety as picomolar inhibitors of cytosolic CA I and CA II isoforms
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Abstract A series of potent inhibitors of human carbonic anhydrase (CA) isoforms I and II has been prepared via a direct, chemoselective sulfochlorination of a range of 1,3-oxazolyl benzenes and thiophenes, followed by primary sulfonamide synthesis. The latter functionality is a known zinc-binding group (ZBG) responsible for anchoring the inhibitors to the CA's zinc metal ion. The compound's periphery as well as the overall scaffold geometry was designed to enable optimal interactions with the two distinct sides of the enzyme's active site, one of which is lined with hydrophobic residues and while the other is predominantly hydrophilic. As a result, several compounds inhibiting the therapeutically important cytosolic CA I and CA II in picomolar range have been identified. These compounds are one of the most potent CA inhibitors identified to-date. Not only the remarkable (>10 000-fold), cytosolic CA I and CA II selectivity vs. the membrane-bound CA IX and CA XII isoforms, but also the pronounced CA II/I selectivity observed in some cases, allow considering this series as a set of isoform-selective chemical biology tools and promising starting points for drug candidate development.
- Krasavin, Mikhail,Korsakov, Mikhail,Dorogov, Mikhail,Tuccinardi, Tiziano,Dedeoglu, Nurcan,Supuran, Claudiu T.
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p. 334 - 347
(2015/07/28)
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- TBAI-catalyzed oxidative cross-coupling of phenols and 2-aminoacetophenones
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An iodide-catalyzed oxidative cross-coupling between phenols and 2-aminoacetophenones has been developed. Using catalytic amounts of tetrabutylammoniumiodide (TBAI) as an iodine-containing catalyst and aqueous solutions of tert-butyl hydro-peroxide (TBHP)
- Xu, Wei,Nachtsheim, Boris J.
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supporting information
p. 1585 - 1588
(2015/03/30)
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- Synthetic studies on mitotic kinesin Eg5 inhibitors: Synthesis and structure-activity relationships of novel 2,4,5-substituted-1,3,4-thiadiazoline derivatives
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The 2,4,5-substituted-1,3,4-thiadiazoline derivative 1a has been identified as a new class of mitotic kinesin Eg5 inhibitor. With the aim of enhancement of the mitotic phase accumulation activity, structure optimization of side chains at the 2-, 4-, and 5
- Yamamoto, Junichiro,Amishiro, Nobuyoshi,Kato, Kazuhiko,Ohta, Yoshihisa,Ino, Yoji,Araki, Mitsuharu,Tsujita, Tetsuya,Okamoto, Seiho,Takahashi, Takeshi,Kusaka, Hideaki,Akinaga, Shiro,Yamashita, Yoshinori,Nakai, Ryuichiro,Murakata, Chikara
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p. 3961 - 3963
(2014/09/17)
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- Discovery and optimization of substituted 1-(1-phenyl-1H-pyrazol-3-yl) methanamines as potent and efficacious type II calcimimetics
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Our efforts to discover potent, orally bioavailable type II calcimimetic agents for the treatment of secondary hyperparathyroidism focused on the development of ring constrained analogues of the known calcimimetic R-568. The structure-activity relationships of various substituted heterocycles and their effects on the human calcium-sensing receptor are discussed. Pyrazole 15 was shown to be efficacious in a rat in vivo pharmacodynamic model.
- Poon, Steve F.,St Jean Jr., David J.,Harrington, Paul E.,Henley III, Charles,Davis, James,Morony, Sean,Lott, Fred D.,Reagan, Jeff D.,Lu, Jenny Ying-Lin,Yang, Yuhua,Fotsch, Christopher
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supporting information; experimental part
p. 6535 - 6538
(2010/04/03)
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- SMALL MOLECULE INHIBITORS OF PLASMODIUM FALCIPARUM DIHYDROOROTATE DEHYDROGENASE
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Inhibitors of dihydroorotate dehydrogenase (DHODH) for the Plasmodium enzyme have been identified and characterized. The inhibitors have high specificity, submicromolar efficacy against cultured parasite strains, exhibit drug-like properties, and are not overtly cytotoxic.
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- Synthesis of novel trisubstituted imidazolines
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Imidazolines substituted at the 1- and either the 4-, or 5-position with phenyl and at the 2-position with alkyl or phenyl have been prepared in racemic form. They appear to be fairly stable compounds and potentially useful as scaffolds in medicinal chemistry. Georg Thieme Verlag Stuttgart.
- Lakner, Frederick J.,Parker, Matthew A.,Rogovoy, Boris,Khvat, Alexander,Ivachtchenko, Alexander
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experimental part
p. 1987 - 1990
(2009/12/25)
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- Synthesis and biological evaluation of imidazol-2-one derivatives as potential antitumor agents
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A new series of aryl substituted imidazol-2-one derivatives structurally related to combretastatin A-4 (CA-4) were synthesized and evaluated for their cytotoxic activities in vitro against various human cancer cell lines including MDR cell line. The cytotoxic effects of compounds 7b and 7i proved to be similar to or greater than that of docetaxel. The highly active compound 7b also exhibited excellent inhibitory activity on tumor growth in vivo.
- Xue, Na,Yang, Xiaochun,Wu, Rui,Chen, Jing,He, Qiaojun,Yang, Bo,Lu, Xiuyang,Hu, Yongzhou
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p. 2550 - 2557
(2008/09/21)
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- A new family of small molecules to probe the reactivation of mutant p53
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Cells that express mutant p53 derived from cancers are selectively killed by a new class of small organic molecules. The protein p53 is recognized as one of the most important guardians in the body that prevents tumor development. Mutant forms of p53 are
- Myers, Michael C.,Wang, JinLing,Iera, Jaclyn A.,Bang, Jeong-Kyu,Saito, Shin'ichi,Hara, Toshiaki,Zambetti, Gerard P.,Appella, Daniel H.
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p. 6152 - 6153
(2007/10/03)
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- COMPOUNDS AND RELATED METHODS FOR MUTANT p53 REACTIVATION
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Ketoamine compounds and related methods for reactivation of tumor suppressor protein p53.
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Page/Page column 27
(2008/06/13)
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- 7-alkyl- and 7-cycloalkyl-5-aryl-pyrrolo[2,3-d]pyrimidines - Potent inhibitors of the tyrosine kinase c-Src
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7-Substituted-5-aryl-pyrrolo[2,3-d]pyrimidines have been prepared starting from α-bromoacetophenones. These compounds represent a novel class of potent inhibitors of the tyrosine kinase pp60c-Src with good specificity towards other tyrosine kinases (EGF-R, v-Abl).
- Widler, Leo,Green, Jonathan,Missbach, Martin,Susa, Mira,Altmann, Eva
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p. 849 - 852
(2007/10/03)
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- Indium metal as a reducing agent in organic synthesis
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The low first ionisation potential (5.8 eV) of indium coupled with its stability towards air and water, suggest that this metallic element should be a useful reducing agent for organic substrates. The use of indium metal for the reduction of C=N bonds in imines, the heterocyclic ring in benzo-fused nitrogen heterocycles, of oximes, nitro compounds and conjugated alkenes and the removal of 4-nitrobenzyl protecting groups is described. Thus the heterocyclic ring in quinolines, isoquinolines and quinoxalines is selectively reduced using indium metal in aqueous ethanolic ammonium chloride. Treatment of a range of aromatic nitro compounds under similar conditions results in selective reduction of the nitro groups; ester, nitrile, amide and halide substituents are unaffected. Likewise indium in aqueous ethanolic ammonium chloride is an effective method for the deprotection of 4-nitrobenzyl ethers and esters. Indium is also an effective reducing agent under non-aqueous conditions and α-oximino carbonyl compounds can be selectively reduced to the corresponding N-protected amine with indium powder, acetic acid in THF in the presence of acetic anhydride or di-tert-butyl dicarbonate. Conjugated alkenes are also reduced by indium in THF-acetic acid.
- Pitts,Harrison,Moody
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p. 955 - 977
(2007/10/03)
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- Elevation of HDL cholesterol by N-[2-[(aminothioxomethyl) hydrazono]-2-arylethyl]amides
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This invention relates to the treatment of atherosclerosis via raising the level of HDL cholesterol by administration of a compound of the formula STR1 wherein: R1, R2, and R3 are independently hydrogen, C1 -C6 alkyl or --(CH2)0-6 Ph where Ph is phenyl op
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- Indium as a reducing agent: Reduction of oximes
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α-Oximino carbonyl compounds can be selectively reduced to the corresponding N-acetyl amine with indium powder, acetic anhydride and acetic acid in THF.
- Harrison,Moody,Pitts
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p. 1601 - 1602
(2007/10/03)
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- Rapid synthesis of oxazoles under microwave conditions
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A new and efficient variation of the Robinson-Gabriel oxazole synthesis is described. Oxazoles were prepared by cyclodehydration of 2-acylamino carbonyl compounds with Burgess reagent under monomode microwave irradiation.
- Brain, Christopher T.,Paul, Jane M.
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p. 1642 - 1644
(2007/10/03)
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- Biotransformations with baker's yeast: pH effects on diastereoselectivity during α-hydroxy-β-ketoester reductions and carbon-carbon bond cleavages
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Baker's yeast mediated reduction of α-substituted-β-ketoesters lead to reduction of the carbonyl group with high enantiospecificity and diastereoselectivity at low pH (4.0-5.0, e.e. >99%, d.e. >90%) but cleavage of the C-C bond is observed at higher pH >8.0). Similar carbon-carbon bond cleavages are observed in the reactions of α-acetamido-β-ketoesters and acetamidocinnamic acid.
- Fadnavis,Kumara Vadivel,Bhalerao
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p. 2355 - 2359
(2007/10/03)
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- Zinc-promoted Reactions. Part 10.1 Reduction of α- and β-Cyano Ketones in Protic and Aprotic Systems
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The difference courses of the zinc-promoted reductions of α- vs.β-cyano ketones in AcOH-Ac2O and CH3CN-CITMS can be interpreted according to a general mechanism.
- Di Vona, Maria Luisa,Rosnati, Vittorio
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p. 498 - 499
(2007/10/03)
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- Investigations of Novel Azomethine Ylide-Forming Photoreactions of N-Silylmethylimides
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The scope of a recently discovered (Yoon, E.C. et al.J.Am.Chem.Soc. 1995, 117, 2698), azomethine ylide-forming photoreaction has been explored by probing the excited state chemistry of several N-trimethylsilylmethyl substituted cyclic and acyclic imides and amide analogs.Photolysis of N-maleimide (4) in acetonitrile leads to efficient production of the tricyclic product 16, formed by trapping of the photogenerated azomethine ylide intermediate 15 through cycloaddition with 4.Irradiation 4 in solutions containing high concentrations of the dipolarophiles, acrylonitrile or fumaronitrile, results in production of the products (19-21 and 23-24, respectively) arising by cycloaddition of the ylide 15 with the added dipolarophiles.In contrast, photolysis of the nonconjugated cyclic imide, N-succinimide (5), brings about N-acyl migration resulting in the exclusive production of the unstable, iminolactone 30.On the other band, acyclic, N-trimethylsilylmethyl aroyl imides 6-8 undergo the excited state C to O silyl migration reaction to produce azomethine ylide intermediates 35.Both in the presence or absence of added dipolarophiles, these ylides undergo electrocyclization to form transient aziridine intermediates 36 which react further by ring opening to generate N-phenacylamide products 32-34.In contrast, the nonconjugated imide, N--N-acetylacetamide (9), is unreactive upon irradiation.Similarly, simple N-amides 10-13, while being photochemically labile, do not react to form "trappable" ylide intermediates upon irradiation.The results outlined above are presented and discussed in terms of the scope and limitations of the new, azomethine ylide-forming photoreaction of silylmethyl imides.
- Yoon, Ung Chan,Cho, Sung Ju,Lee, Yean-Jang,Mancheno, Maria J.,Mariano, Patrick S.
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p. 2353 - 2360
(2007/10/02)
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- Baker's Yeast Reduction of α-(Acylamino)acetophenones and Lipase Catalyzed Resolution of 2-Acylamino-1-arylethanols
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Enzymatic reduction of α-acylaminoacetophenones with fermenting baker's yeast afforded optically active (R)-2-acylamino-1-arylethanols.Furthermore, lipase-catalyzed resolution of the 2-acylamino-1-arylethanols using vinyl acetate as an acyl donor resulted in the formation of (S)-1-acetoxy-2-acylamino-1-arylethanols and (R)-2-acylamino-1-arylethanols.
- Izumi, Taeko,Fukaya, Katsumi
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p. 1216 - 1221
(2007/10/02)
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- Synthesis of 4-oxopyrrolopyrimidine-3-carboxylic acid derivatives as potential antimicrobial agents
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A route for the synthesis of various derivatives of 4-oxopyrrolopyrimidine-3-carboxylic acid from 2-amino-3-cyano-4,5-dimethylpyrrole and 2-amino-3-cyano-4-arylpyrroles is described.
- Bayomi, Said M.,Al-Obaid, Abdul Rahman M.,Jado, Ahmad I.,Loutfy, Essam A.
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p. 814 - 816
(2007/10/02)
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- Reversed-phase liquid chromatographic separation of enantiomeric and diastereomeric bases related to chloramphenicol and thiamphenicol.
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The important antimicrobial agents chloramphenicol and thiamphenicol are N-acylated amines whose chemical structures include two chiral centers. Each drug is the single enantiomer of R,R configuration. The N-deacylated bases of the drugs are important intermediates in their synthesis and optical resolution. In this report, reversed-phase HPLC methods are described for the separation of enantiomeric and diastereomeric bases of the two drugs and of two closely related bases used in some syntheses of the drugs. The stereoisomeric bases were derivatized with a homochiral isothiocyanate and the resulting diastereomeric thioureas were separated on C18 columns with methanol:water mixtures as mobile phases and detection at 254 nm. The four stereoisomeric bases of chloramphenicol and those of its unnitrated analogue were thus separable after derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate. This reagent also allowed the separation of the D-threo isomer of the p-mercaptomethyl analogue of thiamphenicol base from its stereoisomers. The stereoisomers of thiamphenicol base were similarly separated with (R)-alpha-methylbenzyl isothiocyanate as the derivatizing agent. The diastereomers of chloramphenicol base and of thiamphenicol base were chromatographically separable after derivatization with the nonchiral reagent benzyl isothiocyanate. The procedures developed may be useful in the determination of the stereoisomeric composition of the drugs in research and in quality control, and may be applicable to other similar agents whose chemistry and pharmacology are receiving considerable attention.
- Gal,Meyer-Lehnert
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p. 1062 - 1065
(2007/10/02)
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- Total Synthesis of (+/-) Resedine and (+/-)Resedinine Alkaloids from Reseda luteola
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Total synthesis of racemic alkaloids: resedine and resedinine is described.
- Mieczkowski, Jozef B.
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p. 109 - 113
(2007/10/02)
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- 4(1H)-Oxocinnoline-3-carboxylic acid derivatives
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Amide and ester derivatives of substituted-4(1H)-oxocinnoline-3-carboxylic acids have antibacterial activity and are useful for inhibiting the growth of disease causing bacteria.
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