- Process development and pilot-scale synthesis of new cyclization conditions of substituted phenylacetamides to tetrahydroisoquinoline-2-ones using Eaton's reagent
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Tetrahydroisoquinoline is a ubiquitous structural framework presented in numerous pharmacologically relevant molecules. Although accessible by the Pictet-Spengler cyclization, conditions commonly used for such cyclizations are often difficult to implement on scale. Herein, we report the development of a scaleable approach utilizing Eaton's reagent for the cyclization of substituted phenylacetamide analogues to tetrahydroisoquinoline-2-one. The development, optimization, and safety hazard evaluations, which outline the benefits and ease of workup of this new process, are discussed.
- Ulysse, Luckner G.,Yang, Qiang,McLaws, Mark D.,Keefe, Daniel K.,Guzzo, Peter R.,Haney, Brian P.
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- Synthesis and antimicrobial activity of some novel 2-(p-substituted-phenyl)-5-substituted-carbonylaminobenzoxazoles.
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A series of 2-(p-substituted-phenyl)-5-substituted-carbonylamino benzoxazole derivatives (5-22) was synthesized and their antimicrobial activities determined in comparison to several control drugs. The synthesized compounds were tested in vitro against Staphylococcus aureus, Streptococcus faecalis and Bacillus subtilis as Gram-positive, Pseudomonas aeruginosa and Escherichia coli as Gram-negative bacteria and the yeast Candida albicans. Microbiological results showed that the compounds possessed a diffuse spectrum of antibacterial activity against these microorganisms. Compound 9 which bears a phenylacetamido moiety at position 5 and a 4-fluorophenyl group at the 2-position of benzoxazole ring was the most active derivative against S. aureus, S. faecalis and P. aeruginosa with a MIC value of 12.5 microg/ml. Compound 11 provided higher potency than the other tested compounds against B. subtilis at a MIC value of 12.5 microg/ml. Compounds 5-22 showed antifungal activity against C. albicans with MIC values between 50 and 12.5 microg/ml.
- Arpaci, Ozlem Temiz,Oren, Ilkay,Altanlar, Nurten
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- Direct meta-C?H Perfluoroalkenylation of Arenes Enabled by a Cleavable Pyrimidine-Based Template
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The development of efficient and mild methods for the synthesis of organofluorine compounds is of foremost interest in various fields of chemistry. A direct pyrimidine-based selective meta-C?H perfluoroalkenylation of arenes involving several commercially
- Brochetta, Massimo,Borsari, Tania,Bag, Sukdev,Jana, Sadhan,Maiti, Siddhartha,Porta, Alessio,Werz, Daniel B.,Zanoni, Giuseppe,Maiti, Debabrata
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- Antifungal, Phytotoxic, and Cytotoxic Activities of Metabolites from Epichlo bromicola, a Fungus Obtained from Elymus tangutorum Grass
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The development of high-quality herbage is an important aspect of animal husbandry. Inoculating beneficial fungi onto inferior grass is a feasible strategy for producing new varieties of high-quality herbage. Epichlo bromicola is a candidate fungus that i
- Song, Qiu-Yan,Nan, Zhi-Biao,Gao, Kun,Song, Hui,Tian, Pei,Zhang, Xing-Xu,Li, Chun-Jie,Xu, Wen-Bo,Li, Xiu-Zhang
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- Synthesis and antimicrobial activity of new 2-[p-substituted-benzyl]-5- [substituted-carbonyl-amino]benzoxazoles
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A series of 23 new 2-[p-substituted-benzyl]-5-[p-substituted-phenyl/benzyl- carbonylamino]benzoxazole derivatives has been synthesized by reacting 5-amino-2-[p-substituted-benzyl]benzoxazoles with the appropriate carboxylic acid chlorides. The structures of the synthesized compounds were confirmed by IR and 1H-NMR spectral data. Antimicrobial activities of the compounds were investigated using the twofold serial dilution technique against two gram-positive and two gram-negative bacteria and three Candida species in comparison with standard drugs. Microbiological results indicated that the newly synthesized 2-[p-substituted-benzyl]-5-[p-substituted-phenyl/benzyl- carbonylamino]benzoxazole derivatives (3-25) possessed a broad spectrum of activity, showing MIC values of 6.25-200 μg/mL against the gram-positive and gram-negative microorganisms tested. Moreover, they showed significant antifungal activity with MIC values of 3.12-100 μg/mL against the Candida species tested. Especially, with a MIC value of 3.12 μg/mL, 2-benzyl-5-[p-bromobenzyl-carbonylamino]benzoxazole 9 displayed the same activity against C. glabrata as the standard drug myconazol.
- Yildiz-Orena, Ilkay,Tekiner-Gulbas, Betul,Yalcin, Ismail,Temiz-Arpaci, Ozlem,Aki-Sener, Esin,Altanlar, Nurten
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- Solution and solid-state models of peptide CH...O hydrogen bonds
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Fumaramide derivatives were analyzed in solution by 1H NMR spectroscopy and in the solid state by X-ray crystallography in order to characterize the formation of CH...O interactions under each condition and to thereby serve as models for these interactions in peptide and protein structure. Solutions of fumaramides at 10 mM in CDCl3 were titrated with DMSO-d6, resulting in chemical shifts that moved downfield for the CH groups thought to participate in CH...O=S(CD3)2 hydrogen bonds concurrent with NH...O=S(CD3)2 hydrogen bonding. In this model, nonparticipating CH groups under the same conditions showed no significant change in chemical shifts between 0.0 and 1.0 M DMSO-d6 and then moved upfield at higher DMSO-d6 concentrations. At concentrations above 1.0 M DMSO-d6, the directed CH...O=S(CD3)2 hydrogen bonds provide protection from random DMSO-d6 contact and prevent the chemical shifts for participating CH groups from moving upfield beyond the original value observed in CDCl3. X-ray crystal structures identified CH...O=C hydrogen bonds alongside intermolecular NH...O=C hydrogen bonding, a result that supports the solution 1H NMR spectroscopy results. The solution and solid-state data therefore both provide evidence for the presence of CH...O hydrogen bonds formed concurrent with NH...O hydrogen bonding in these structures. The CH...O=C hydrogen bonds in the X-ray crystal structures are similar to those described for antiparallel β-sheet structure observed in protein X-ray crystal structures.
- Baures, Paul W.,Beatty, Alicia M.,Dhanasekaran, Muthu,Helfrich, Brian A.,Perez-Segarra, Waleska,Desper, John
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- Comparative reactivity of N′-(5-benzoyl/ethoxycarbonyl)thiazol-2-yl- N,N-dimethylformamidines with ketenes
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The comparative account of the reactivities of N′-[(5-benzoyl and ethoxycarbonyl)thiazol-2-yl]-N,N-dimethylformamidines (1a and 1b), tremendously influenced by the electronic nature of the substituents on C-5 of the thiazolic ring with various monosubstituted and conjugated ketenes is reported herein. The DA cycloadditions of the dienyl pyrimidinone 3h with both symmetrical as well as unsymmetrical dienophiles leading to the formation of various thiazolic pyrimidinone derivatives are also reported.
- Singh, Parvesh,Marwaha, Alka,Singh, Harmeet,Mahajan, Mohinder P.
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- Photochemistry of N-hydroxypyridine-2-thione derivatives: Involvement of the 2-pyridylthiyl radical in the radical chain reaction mechanism
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The primary and subsequent photochemistry of four N-hydroxypyridine-2-thione esters has been investigated by laser flash photolysis (λexc = 355 nm). A simple, high-yield synthetic method is given for their preparation with high purity. UV irradiation of these ester compounds was shown to lead specifically to the formation of benzyl, diphenylmethyl, tert-butyl, and benzoyloxyl radicals in addition to the 2-pyridylthiyl radical. In all cases, the initial photoinduced nitrogen-oxygen bond cleavage was found to occur in high quantum yield (ΦN-O ≈ 0.5). The radical species generated by this process (2-pyridylthiyl radical and carbon-centered or oxygen-centered radicals) were characterized and their reactivity toward several radical scavengers has been studied. An efficient delayed depletion of the N-hydroxypyridine-2-thione esters was also observed, leading to overall bleaching quantum yields, ΦBl, close to unity. We have demonstrated that the delayed consumption of ground-state ester was due to the reaction of the 2-pyridylthiyl radical with its precursor, occurring with a rate constant, kr, of 3-4 × 109 M-1 s-1. This reaction, hitherto never proposed, leads to the formation of 2,2′-dipyridyl disulfide and further release of propagating radicals.
- Aveline, Béatrice M.,Kochevar, Irene E.,Redmond, Robert W.
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- A simple method for the microscale preparation of Mosher's acid chloride
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Mosher's acid is treated with oxalyl chloride in the presence of DMF in hexane. Filtration and concentration provide the acid chloride which is suitable for use without further purification. The procedure is amenable to microscale.
- Ward,Rhee
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- Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
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Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
- Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
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supporting information
p. 5022 - 5037
(2021/05/04)
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- One-step Conversion of Amides and Esters to Acid Chlorides with PCl3
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A general and efficient iodine-promoted chlorination of amides and esters with phosphorus trichloride is described. For the first time. Various inactivated amides including secondary and tertiary amides were directly converted to the corresponding acid chlorides in one-step. The substrate scope of methyl esters including aromatic and aliphatic esters was also explored under this system. This method is simple, scalable and wide in scope, which provides an approach to preparation of these acid chlorides.
- Li, Fangshao,Wu, Xiaofang,Guo, Fengzhe,Tang, Zi-Long,Xiao, Jing
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supporting information
p. 4314 - 4317
(2021/07/16)
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- Carbon dots as photocatalysts for organic synthesis: Metal-free methylene-oxygen-bond photocleavage
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We report for the first time that irradiation of four different citric acid-derived carbon dots (CDs), in the absence of any other redox mediators, promotes an organic reaction. In this proof-of-concept study methylene-oxygen bond reductive photocleavage in N-methyl-4-picolinium esters is demonstrated. Cyclic voltammetry and UV-Vis spectra of the CDs and of the esters indicate that photocleavage reactivity correlates with the redox properties and the relative energies expressed in the Fermi scale. A photo-fragmentation mechanism is proposed. This study offers a new possibility to employ inexpensive and readily available CDs to promote photo-organic reactions.
- Cailotto, Simone,Negrato, Matteo,Daniele, Salvatore,Luque, Rafael,Selva, Maurizio,Amadio, Emanuele,Perosa, Alvise
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supporting information
p. 1145 - 1149
(2020/03/11)
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- Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class i HDAC Enzymes and Cancer Cell Proliferation
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AR-42 is an orally active inhibitor of histone deacetylases (HDACs) in clinical trials for multiple myeloma, leukemia, and lymphoma. It has few hydrogen bond donors and acceptors but is a chiral 2-arylbutyrate and potentially prone to racemization. We report achiral AR-42 analogues incorporating a cycloalkyl group linked via a quaternary carbon atom, with up to 40-fold increased potency against human class I HDACs (e.g., JT86, IC50 0.7 nM, HDAC1), 25-fold increased cytotoxicity against five human cancer cell lines, and up to 70-fold less toxicity in normal human cells. JT86 was ninefold more potent than racAR-42 in promoting accumulation of acetylated histone H4 in MM96L melanoma cells. Molecular modeling and structure-activity relationships support binding to HDAC1 with tetrahydropyran acting as a hydrophobic shield from water at the enzyme surface. Such potent inhibitors of class I HDACs may show benefits in diseases (cancers, parasitic infections, inflammatory conditions) where AR-42 is active.
- Tng, Jiahui,Lim, Junxian,Wu, Kai-Chen,Lucke, Andrew J.,Xu, Weijun,Reid, Robert C.,Fairlie, David P.
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p. 5956 - 5971
(2020/06/05)
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- Visible light-induced transformation of aldehydes to esters, carboxylic anhydrides and amides
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A transition metal- and organophotocatalyst free synthesis of esters, carboxylic anhydrides and amides from aldehydes induced by visible-light has been reported. The proposed methodology can be carried out by the use of sunlight or artificial visible light as a blue LED source. The methodology has a very broad applicability and the desired products are obtained in very satisfactory yields.
- Gaspa, Silvia,Raposo, Inês,Pereira, Leonor,Mulas, Gabriele,Ricci, Pier Carlo,Porcheddu, Andrea,De Luca, Lidia
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supporting information
p. 10711 - 10715
(2019/07/15)
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- Preparation technology of atorvastatin
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The invention discloses preparation technology of atorvastatin. The preparation technology comprises the following steps: a first step, the reaction of phenylacetic acid and thionyl chloride is carried out in order to obtain phenylacetyl chloride; a second step, the Friedel-Crafts acylation reaction of phenylacetyl chloride and fluorobenzene is carried out under the action of catalyst, in order to obtain 4-fluorophenyl acetophenone; a third step, 4-fluorophenyl acetophenone is brominated and the brominated 4-fluorophenyl acetophenone is reacted with N-phenyl-isobutyloylacetamide in order to obtain M-4; a fourth step, a reaction is carried out for M-4 and ATS-9 in a cyclohexane, toluene or a mixed solvent of cyclohexane and toluene, pivalic acid is used for catalysis, and a condensation product is obtained. Phenylacetyl chloride and fluorobenzene are reacted in a catalytic action of zeolite molecular sieve, a complexation reaction of the catalyst and products is avoided, reaction yield is improved, and side reactions are few in order to facilitate purification; post-treatment can be carried out for excess M-4 for recycling and reusing, reaction yield is improved, mole proportion of M-4 to ATS-9 and the addition amount of pivalic acid can be adjusted, and final yield of the reaction is improved.
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Paragraph 0018; 0019; 0024; 0025; 0030; 0031; 0036; 0037
(2017/08/27)
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- An anti-choline medicine preparation method of atropine sulfate
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The invention provides a synchronizing method of atropine sulphate. The method is characterized in that hydrolyzing methyl phenoxyacetate (II) is hydrolyzed to obtain a compound (III); the compound (III) and thionyl chloride are subjected to acylation reaction to obtain a compound (IV); the compound (IV) and 8-methyl-8-azabicyclo[3.2.1]oct-3-alchol are subjected to condensation reaction to obtain a compound (V); the compound (V) and paraformaldehyde are used for producing atropine (VI) under an alkaline condition; the atropine (VI) is salified under an acidic condition to obtain the atropine sulphate (I). The preparation method is simple in technology, high in yield, high in purity, low in monomer impurity and easy for industrial production.
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Paragraph 0033; 0034
(2017/03/08)
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- Α-chloro -4 fluoro phenyl benzylone method for the synthesis of
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The invention relates to the field of chemistry, particularly to the field of medicinal chemistry, more particularly to a synthetic method for alpha-chlorine-4fluorine phenyl benzyl ketone, and aims to solve the problems that in the traditional preparation technology, the cost for preparing phenylacetic acid synthetic compound is high, the technology is complicated and the technology is not suitable for industrial production. The invention provides a novel synthetic method for alpha-chlorine-4fluorine phenyl benzyl ketone through adopting mandelic acid, which includes the following steps: alpha position chloro takes as the first step reaction, corresponding synthetic parameters are matched, and the mandelic acid takes as a starting material for synthesizing compound (4). Therefore, the total yield reaches 67.8% after three-step synthesis, by-products generated in the reaction are reduced, the purity of a target object is high, the purification is easy, and the method is suitable for industrial production.
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Paragraph 0037
(2017/04/28)
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- Proline compounds as Granzyme B inhibitors
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Proline compounds as Granzyme B inhibitors, compositions that include the compounds, and methods for using the compounds. Methods for treating cutaneous scleroderma, epidermolysis bullosa, radiation dermatitis, alopecia areata, and discoid lupus erythematosus are provided.
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- Metal-Free Direct Oxidation of Aldehydes to Esters Using TCCA
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Aromatic and aliphatic aldehydes are simply converted into esters by an efficient oxidative esterification carried out under mild conditions. The aldehydes are converted in situ into their corresponding acyl chlorides, which are then reacted with primary and secondary aliphatic, benzylic, allylic, and propargylic alcohols and phenols. A variety of esters are obtained in high yields.
- Gaspa, Silvia,Porcheddu, Andrea,De Luca, Lidia
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supporting information
p. 3666 - 3669
(2015/08/18)
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- SUBSTITUTED BENZOTHIAZOLES AND THERAPEUTIC USES THEREOF FOR THE TREATMENT OF HUMAN DISEASES
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The invention relates to a family of differently substituted benzothiazoles having an inhibitory activity against the enzyme casein kinase 1 (CK1), as a result of which they are suitable for use in the treatment or prevention of diseases caused by this enzyme, particularly diseases associated with circadian rhythm and inflammatory, autoimmune, psychiatric, neurodegenerative, neurological or ophthalmological diseases, as well as for inducing cell regeneration.
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Paragraph 0087
(2015/12/18)
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- Cu-Catalyzed cascades to carbocycles: Union of diaryliodonium salts with alkenes or alkynes exploiting remote carbocations
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Copper-catalyzed cascade reactions between alkenes or alkynes and diaryliodonium salts form carbocyclic products in a single step. Arylation of the unsaturated functional group is proposed to form a carbocation intermediate that facilitates hydride shift pathways to translocate the positive charge to a remote position and enables ring formation via a Friedel-Crafts-type reaction.
- Zhang, Fengzhi,Das, Shoubhik,Walkinshaw, Andrew J.,Casitas, Alicia,Taylor, Michael,Suero, Marcos G.,Gaunt, Matthew J.
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supporting information
p. 8851 - 8854
(2014/07/08)
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- COSMETIC USES AND METHODS FOR INDOLINE GRANZYME B INHIBITOR COMPOSITIONS
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Cosmetic uses and methods for indoline granzyme B inhibitor compounds in compositions with a cosmetically acceptable carrier. Uses and methods for treating, reducing or inhibiting the appearance of ageing in the skin are provided. Also provided are compositions and formulation for cosmetic uses and methods of maintaining a youthful appearance, reducing an appearance of ageing, inhibiting an appearance of ageing, reducing a rate of an appearance of ageing, reducing a skin inelasticity, reducing a rate of increasing skin inelasticity, maintaining a skin elasticity, and increasing the density of hair follicles of a skin of a subjecl. The uses and methods comprise applying/administering an indoline granzyme B inhibitor to a skin, or a portion of a skin of the subject.
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- Copper-catalyzed carboarylation of alkynes via vinyl cations
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Copper-catalyzed arylation of electron rich alkynes reveals stabilized trisubstituted vinyl cation equivalents that react with pendant arene nucleophiles to form all carbon tetrasubstituted alkenes. The new process streamlines the synthesis of important medicinally relevant molecules.
- Walkinshaw, Andrew J.,Xu, Wenshu,Suero, Marcos G.,Gaunt, Matthew J.
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supporting information
p. 12532 - 12535
(2013/09/23)
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- Ethanesulfohydroxamic acid ester prodrugs of nonsteroidal anti-inflammatory drugs (NSAIDs): Synthesis, nitric oxide and nitroxyl release, cyclooxygenase inhibition, anti-inflammatory, and ulcerogenicity index studies
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The carboxylic acid group of the anti-inflammatory (AI) drugs indo-methacin, (S)-naproxen and ibuprofen was covalently linked via a two-carbon ethyl spacer to a sulfohydroxamic acid moiety (CH2CH 2SO2NHOH) to furnish a group of hybrid ester prodrugs that release nitric oxide (NO) and nitroxyl (HNO). Biological data acquired for this hitherto unknown class of ethanesulfohydroxamic acid ester prodrugs showed (i) all compounds exhibited superior NO, but similar HNO, release properties relative to arylsulfohydroxamic acids, (ii) the (S)-naproxen and ibuprofen prodrug esters are more potent AI agents than their parent NSAID, (iii) the indomethacin prodrug ester, in contrast to indomethacin which is highly ulcerogenic, showed no visible stomach lesions [ulcer index (UI) = 0 for a 80 μmol/kg oral dose] while retaining potent AI activity, and iv) that the indomethacin prodrug ester, unlike indomethacin which is an ulcerogenic selective COX-1 inhibitor, is a selective COX-2 inhibitor (COX-2 selectivity index = 184) devoid of ulcerogenicity that is attributed to its high COX-2 SI and/or ability to release cytoprotective NO.
- Huang, Zhangjian,Velázquez, Carlos A.,Abdellatif, Khaled R. A.,Chowdhury, Morshed A.,Reisz, Julie A.,Dumond, Jenna F.,King, S. Bruce,Knaus, Edward E.
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experimental part
p. 1356 - 1364
(2011/04/24)
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- Valence tautomerism in titanium enolates: Catalytic radical haloalkylation and application in the total synthesis of neodysidenin
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(Chemical Equation Presented) A direct ruthenium-catalyzed radical chloroalkylation of N-acyl oxazolidinones capitalizing on valence tautomerism of titanium enolates has been developed. The chloroalkylation method served as the centerpiece in the enantioselective total synthesis of trichloroleucine-derived marine natural product neodysidenin.
- Beaumont, Stephane,Ilardi, Elizabeth A.,Monroe, Lucas R.,Zakarian, Armen
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supporting information; experimental part
p. 1482 - 1483
(2010/04/03)
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- Synthesis and PGE2 production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives
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3,4-Diphenyl-substituted 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives were synthesized and evaluated for the inhibitory activities on LPS-induced PGE2 production in RAW 264.7 macrophage cells. Both 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione rings as main scaffolds were easily obtained using one of three synthetic methods. Among the compounds investigated, 1H-3-(4-sulfamoylphenyl)-4-phenyl-pyrrole-2,5-dione (6l) showed a strong inhibitory activity (IC50 = 0.61 μM) of PGE2 production.
- Moon, Jong Taik,Jeon, Ji Young,Park, Hang Ah,Noh, Young-Soo,Lee, Kyung-Tae,Kim, Jungahn,Choo, Dong Joon,Lee, Jae Yeol
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scheme or table
p. 734 - 737
(2010/06/22)
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- Syntheses and evaluation of anticonvulsant profile and teratogenicity of novel amide derivatives of branched aliphatic carboxylic acids with 4-aminobenzensulfonamide
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Despite the availability of 14 new antiepileptic drugs (AEDs), about 30% of epileptic patients are not seizure-free. Consequently there is substantial need to develop new effective AEDs. A novel class of aromatic amides composed of phenylacetic acid or branched aliphatic carboxylic acids, with five to nine carbons in their carboxylic moiety, and aminobenzenesulfonamide were synthesized and evaluated in the anticonvulsant rat-maximal electroshock (MES) and subcutaneous metrazol seizure (scMet) tests. Fourteen of the synthesized amides had an anticonvulsant ED50 of 50 values of 7.6, 9.9, and 9.4 mg/kg and remarkable protective index (PI = TD 50/ED50) values of 65.7, 50.5, and 53.2, respectively. These potent sulfanylamides caused neural tube defects only at doses markedly exceeding their effective dose. The anticonvulsant properties of these compounds make them potential candidates for further development as new, potent, and safe AEDs.
- Hen, Naama,Bialer, Meir,Wlodarczyk, Bogdan,Finnell, Richard H.,Yagen, Boris
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scheme or table
p. 4177 - 4186
(2010/09/04)
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- Design, synthesis and evaluation of 2-amino-4-m-bromoanilino-6-arylmethyl- 7H-pyrrolo[2,3-d]pyrimidines as tyrosine kinase inhibitors and antiangiogenic agents
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A series of 2-amino-4-m-bromoanilino-6-benzyl pyrrolo[2,3-d]pyrimidines analogues 4-12 were synthesized and evaluated as inhibitors of receptor tyrosine kinases (RTKs). These analogues were synthesized from the appropriate α-bromomethylbenzylketones via cyclocondensation with 2,6-diamino-4- pyrimidone to afford the 2-amino-4-oxo-6-substituted benzyl pyrrolo[2,3-d] pyrimidines. Chlorination at the 4-position followed by displacement with 3-bromoaniline or 3-bromo-N-methylaniline and methylation of the 7-NH afforded the target compounds. Remarkably, dimethylation of both the 4-N and N7 afford whole cell EGFR inhibitors that are more cytotoxic than clinically used erlotinib and mono-methylation at the 4-N or N7 affords more cytotoxic whole cell PDGFR-β inhibitors than clinically used sunitinib. Methylation at either the 4-N or N7 position was detrimental to whole cell VEGFR-2 inhibition. The inhibitory data against the RTKs in this study demonstrates that methylation of the 4-NH and/or the 7-NH influences both the specificity and potency of RTK inhibition.
- Gangjee, Aleem,Zhao, Ying,Raghavan, Sudhir,Ihnat, Michael A.,Disch, Bryan C.
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experimental part
p. 5261 - 5273
(2010/09/11)
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- Synthesis of a series of novel 2,4,5-trisubstituted selenazole compounds as potential PLTP inhibitors
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Based on a homology-modeled structure of PLTP and characteristic structural features of reported cholesteryl ester transfer protein (CETP) inhibitors, we designed and synthesized a novel series of 2,4,5-trisubstituted selenazole compounds. Biological evaluation reveals that compounds 12 and 17 exhibit favorable PLTP activity, and their IC50s are 8 μM and 10 μM, respectively.
- Ling, Cui,Zheng, Zhibing,Jiang, Xian Cheng,Zhong, Wu,Li, Song
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scheme or table
p. 5123 - 5125
(2010/10/19)
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- Exalted resonance demands in the substituent effects on the acetolyses of 2-arylethyl trifluoromethanesulfonates destabilized by cn and cf3 groups
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Substituent effects on the acetolysis rates of 2-aryl-l-cyano-l- (trifluoromethyl)ethyl trifluoromethanesulfonates (α-OTf) and 2-aryl-2-cyano-2-(trifluoromethyl)ethyl trifluoromethanesulfonates (ss-OTf) were investigated by using LArSR equation. The obtained p and r+ values were p = -3.28, r+ = 0.98 and p = -3.48,r+ = 0.93 for the acetolysis of α-OTf and ss-OΥi, respectively. The obtained p values are comparable to those for typical aryl-assisted solvolyses, but the r+ values are much larger. The large r+ values suggest that the ester bond cleavages in the deactivated aryl-assisted solvolyses are assisted by the strong participation of the ss-aryl group.
- Usui, Satoshi,Tsuboya, Shoko,Umezawa, Yukthiro,Hazama, Ken,Okamura, Mutsuo
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experimental part
p. 254 - 260
(2009/05/30)
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- Amide-containing diketoacids as HIV-1 integrase inhibitors: Synthesis, structure-activity relationship analysis, and biological activity
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HIV-1 integrase, which catalyzes the integration of the viral genome into the cellular chromosome, is an essential enzyme for retroviral replication, and represents an attractive and validated target in the development of therapeutics against AIDS. In this paper, 17 amide-containing novel diketoacids were designed and synthesized, and their ability to inhibit HIV-1 integrase was tested. The structure-activity relationships were also analyzed.
- Li, Hongcai,Wang, Chao,Sanchez, Tino,Tan, Yanmei,Jiang, Chunying,Neamati, Nouri,Zhao, Guisen
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experimental part
p. 2913 - 2919
(2009/09/06)
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- An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: A facile synthesis of Pyrrolo-tetrahydroisoquinolones and Pyrrolo-benzazepinones
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The triflic acid-mediated cyclisation of N-arylmethyl- and N-arylethyl-acylpyrrolidinium ions gave moderate to good yields of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones respectively. Electron-donating R substituents enhanced the rate of reaction and gave higher yields than electron-withdrawing substituents. Substituents on the methyl or ethyl chain in general enhanced the reaction, unless sterically encumbered. The equivalent acylpiperidinium ions cyclised much slower and in lower yield.
- King, Frank D.,Aliev, Abil E.,Caddick, Stephen,Copley, Royston C. B.
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experimental part
p. 3561 - 3571
(2010/01/06)
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- Synthesis and pharmacological screening of several aroyl and heteroaroyl selenylacetic acid derivatives as cytotoxic and antiproliferative agents
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The synthesis and cytotoxic activity of a series of twenty six aroyl and heteroaroyl selenylacetic acid derivatives of general formula Ar-CO-Se-CH2-COOH or Heterar-CO-Se-CH2-COOH are reported. The synthesis was carried out by reaction of acyl chlorides with sodium hydrogen selenide, prepared in situ, and this led to the formation of sodium aroylselenides that subsequently reacted with --bromoacetic acid to produce the corresponding selenylacetic acid derivatives. All of the compounds were tested against a prostate cancer cell line (PC-3) and some of the more active compounds were assessed against a panel of four human cancer cell lines (CCRF-CEM, HTB-54, HT-29, MCF-7) and one mammary gland-derived non-malignant cell line (184B5). Some of the compounds exhibited remarkable cytotoxic and antiproliferative activities against MCF-7 and PC-3 that were higher than those of the reference compounds doxorubicin and etoposide, respectively. For example, in MCF-7 when Ar=phenyl, 3,5-dimethoxyphenyl or benzyl the TGI values were 3.69, 4.18 and 6.19 -M. On the other hand, in PC-3 these compounds showed values of 6.8, 4.0 and 2.9 -M. Furthermore, benzoylselenylacetic acid did not provoke apoptosis nor did it perturb the cell cycle in MCF-7.
- Sanmartin, Carmen,Plano, Daniel,Dominguez, Enrique,Font, Maria,Calvo, Alfonso,Prior, Celia,Encio, Ignacio,Palop, Juan Antonio
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scheme or table
p. 3313 - 3338
(2010/03/04)
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- Antimalarial and antitrypanosomal activity of a series of amide and sulfonamide derivatives of a 2,5-diaminobenzophenone
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Here, we describe a series of readily obtainable benzophenone derivatives with antimalarial and antitrypanosomal activity. The most active compounds display submicromolar activity against Plasmodium falciparum. Micromolar activity is obtained against Trypanosoma brucei. Main problem of the compounds is low selectivity. However, there are indications that separation of antimalarial and cytotoxic activity might by possible. In addition, some compounds inhibit human ABC transporter with nanomolar activity.
- Altenkaemper, Mirko,Bechem, Benjamin,Perruchon, Johann,Heinrich, Swetlana,Maedel, Andrea,Ortmann, Regina,Dahse, Hans-Martin,Freunscht, Ellen,Wang, Yulin,Rath, Jennifer,Stich, August,Hitzler, Manuela,Chiba, Peter,Lanzer, Michael,Schlitzer, Martin
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experimental part
p. 7690 - 7697
(2010/03/24)
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- Discovery and biological evaluation of novel cyanoguanidine P2X7 antagonists with analgesic activity in a rat model of neuropathic pain
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We disclose the design of a novel series of cyanoguanidines that are potent (IC50 ? 10-100 nM) and selective (≥100-fold) P2X7 receptor antagonists against the other P2 receptor subtypes such as the P2Y2, P2X4, and P2X3. We also found that these P2X7 antagonists effectively reduced nociception in a rat model of neuropathic pain (Chung model). Particularly, analogue 53 proved to be effective in the Chung model, with an ED50 of 38 μmol/kg after intraperitoneal administration. In addition compound 53 exhibited antiallodynic effects following oral administration and maintained its efficacy following repeated administration in the Chung model. These results suggest an important role of P2X7 receptors in neuropathic pain and therefore a potential use of P2X7 antagonists as novel therapeutic tools for the treatment of this type of pain.
- Perez-Medrano, Arturo,Donnelly-Roberts, Diana L.,Honore, Prisca,Hsieh, Gin C.,Namovic, Marian T.,Peddi, Sridhar,Shuai, Qi,Wang, Ying,Faltynek, Connie R.,Jarvis, Michael F.,Carroll, William A.
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experimental part
p. 3366 - 3376
(2010/04/03)
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- Synthesis, antileukemic and antiplatelet activities of 2,3-diaryl-6,7-dihydro-5H-1,4-diazepines
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The synthesis, antileukemic and antiplatelet activity evaluation of 2,3-diaryl-6,7-dihydro-5H-1,4-diazepines are described. In general, it was found that compound 17o showed moderate antileukemic activity against MOLT3 human leukemic cancer cell lines. An arachidonic acid induced platelet aggregation effect on washed rat platelets was studied. Compound 17i was found to be the most potent. The antiplatelet properties may be mediated by interference with the arachidonic acid pathway.
- Ramajayam,Giridhar, Rajani,Yadav,Balaraman,Djaballah, Hakim,Shum, David,Radu, Constantin
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p. 2004 - 2010
(2008/12/22)
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- Novel 3-phenylpropane-1,2-diamine derivates as inhibitors of aminopeptidase N (APN)
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Aminopeptidase N (APN) is an essential peptidase involved in the process of tumor invasion and metastasis. Here we describe a novel class of inhibitor with 3-phenylpropane-1,2-diamine as scaffold to APN. Preliminary activity evaluation with enzyme inhibition studies showed that compound 12i exhibited potent and selective inhibitory activity towards APN with the IC50 value 15.5 ± 1.2 μM.
- Shang, Luqing,Wang, Qiang,Fang, Hao,Mu, Jiajia,Wang, Xuejian,Yuan, Yumei,Wang, Binghe,Xu, Wenfang
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scheme or table
p. 9984 - 9990
(2009/04/06)
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- One-pot synthesis of 2-substituted benzoxazoles directly from carboxylic acids
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Methanesulfonic acid has been found to be a highly effective catalyst for a convenient and one-pot synthesis of 2-substituted benzoxazoles by the reaction of 2-aminophenol with acid chlorides, generated in situ from carboxylic acids. Aryl, heteroaryl, and arylalkyl carboxylic acids provided excellent yields of the corresponding benzoxazoles. The reaction conditions were compatible with various substituents such as chloro, bromo, nitro, methoxy, cyclopentyloxy, phenoxy, thiophenoxy, and conjugated double bonds. Benzoxazole formation was found to be general with respect to substituted 2-aminophenols.
- Kumar, Dinesh,Rudrawar, Santosh,Chakraborti, Asit K.
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body text
p. 881 - 887
(2009/04/11)
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- Heteroaryl β-tetralin ureas as novel antagonists of human TRPV1
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We report on a series of α-substituted-β-tetralin-derived and related phenethyl-based isoquinolinyl and hydroxynaphthyl ureas as potent antagonists of the human TRPV1 receptor. The synthesis and Structure-activity relationships (SAR) of the series are described.
- Jetter, Michele C.,Youngman, Mark A.,McNally, James J.,McDonnell, Mark E.,Zhang, Sui-Po,Dubin, Adrienne E.,Nasser, Nadia,Codd, Ellen E.,Flores, Christopher M.,Dax, Scott L.
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p. 6160 - 6163
(2008/03/18)
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- Synthesis and SAR of succinamide peptidomimetic inhibitors of cathepsin S
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Peptidic, non-covalent inhibitors of lysosomal cysteine protease cathepsin S (1 and 2) were investigated due to low oral bioavailability, leading to an improved series of peptidomimetic inhibitors. Utilizing phenyl succinamides as the P2 residue increased the oral exposure of this lead series of compounds, while retaining selective inhibition of the cathepsin S isoform. Concurrent investigation of the P1 and P2 subsites resulted in the discovery of several potent and selective inhibitors of cathepsin S with good pharmacokinetic properties due to the elimination of saturated aliphatic P2 residues.
- Chatterjee, Arnab K.,Liu, Hong,Tully, David C.,Guo, Jianhua,Epple, Robert,Russo, Ross,Williams, Jennifer,Roberts, Michael,Tuntland, Tove,Chang, Jonathan,Gordon, Perry,Hollenbeck, Thomas,Tumanut, Christine,Li, Jun,Harris, Jennifer L.
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p. 2899 - 2903
(2008/12/22)
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- Evaluation of Zard trifluoromethylketone synthesis for the preparation of potential bifunctional fluorinated synthons
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In the quest for potential bifunctional fluorinated synthons, we examined the behavior of chlorodifluoroacetic and hexafluoroglutaric anhydride in their reaction with acid chlorides in the presence of pyridine under the conditions of Zard trifluoromethylketone synthesis. Chlorodifluoroacetic anhydride led easily to the expected chlorodifluoromethyl ketones in the case of relatively non-encumbered primary acid chlorides. In the case of hexafluoroglutaric anhydride we observed the unexpected formation of α substituted hexafluorocyclohexane-1,3-dione derivatives among with the corresponding fluorinated 3-chloro-cyclohexenones.
- Diter, Patrick,Magnier, Emmanuel,Blazejewski, Jean-Claude
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p. 1235 - 1240
(2008/02/10)
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- Structure-activity relationships in the binding of chemically derivatized CD4 to gp120 from human immunodeficiency virus
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The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.
- Xie, Hui,Ng, Danny,Savinov, Sergey N.,Dey, Barna,Kwong, Peter D.,Wyatt, Richard,Smith III, Amos B.,Hendrickson, Wayne A.
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p. 4898 - 4908
(2008/03/11)
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- Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides
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A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of ortho-haloanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramolecular C-O cross-coupling of the ortho-haloanilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N′- dimethylethylenediamine were shown to provide ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples utilized the cyclization of ortho-bromoanilides, but orthoiodoanilides and ortho-chloroanilides also undergo a reaction under these conditions. The rate of reaction of the ortho-haloanilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.
- Evindar, Ghotas,Batey, Robert A.
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p. 1802 - 1808
(2007/10/03)
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- Discovery of novel hydroxy pyrazole based factor IXa inhibitor
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Synthesis and biological data of a novel selective and efficacious factor IXa inhibitor are described along with its crystal structure in factor VIIa.
- Vijaykumar, Dange,Sprengeler, Paul A.,Shaghafi, Michael,Spencer, Jeffrey R.,Katz, Brad A.,Yu, Christine,Rai, Roopa,Young, Wendy B.,Schultz, Brian,Janc, James
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p. 2796 - 2799
(2007/10/03)
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- Convenient synthesis of N-(4-(2-aminopyridin-4-yl)thiazol-2-yl)-2-phenylacetamides
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We report a facile one-pot, three-step synthesis of N-(4-(2-aminopyridin-4-yl)thiazol-2-yl)-2-phenylacetamides via condensation of 2-p-methoxybenzylamino-4-acetylpyridine with phenylacetylthioureas.
- Bandarage, Upul K.,Come, Jon H.,Green, Jeremy
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p. 8079 - 8081
(2007/10/03)
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- New esters of vanillin and vanillal with some alkane- and arenecarboxylic acids
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Previously unknown esters were synthesized by the reaction of vanillin and vanillal with carboxylic acid chlorides. Pleiades Publishing, Inc., 2006.
- Dikusar
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p. 1035 - 1037
(2008/02/05)
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- Aromatic chlorination of ω-phenylalkylamines and ω- phenylalkylamides in carbon tetrachloride and α,α,α- trifluorotoluene
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The aromatic halogenation of simple alkylbenzenes with chlorine proceeds smoothly in acetic acid but is much less efficient in less polar solvents. By contrast chlorination of ω-phenylalkylamines, such as 3-phenylpropylamine, occurs readily in either acetic acid, carbon tetrachloride or α,α,α-trifluorotoluene, and in the latter solvents gives high proportions of ortho-chlorinated products. These effects are attributable to the involvement of N-chloroamines as reaction intermediates, with intramolecular delivery of the chlorine electrophile. ω-Phenylalkylamides, such as 3-phenylpropionamide, also easily undergo aromatic chlorination in carbon tetrachloride and α,α,α-trifluorotoluene. These reactions generally show a first-order dependence on the substrate concentration, but not on the amount of chlorine. With carbon tetrachloride, very similar reaction rates are observed with chlorine concentrations ranging from 0.1-1.5 M. In α,α,α-trifluorotoluene, the rates reach a plateau at a chlorine concentration of approximately 0.2 M. These features indicate that the reactions proceed via the formation of intermediates which evidence suggests may be the corresponding O-chloroimidates. Irrespective of the mechanistic details, the reactions are remarkably rapid, being faster than analogous reactions in acetic acid and three to four orders of magnitude more rapid than reactions of simple alkylbenzenes in carbon tetrachloride. Therefore, chlorination of the amines and amides may be accomplished without the need for highly polar solvents, added catalysts or large excesses of chlorine, which are often employed for electrophilic aromatic substitutions. Although the use of carbon tetrachloride is becoming increasingly impractical due to environmental concerns, the trifluorotoluene is a suitable alternative. The Royal Society of Chemistry 2006.
- O'Connell, Jenny L.,Simpson, Jamie S.,Dumanski, Paul G.,Simpson, Gregory W.,Easton, Christopher J.
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p. 2716 - 2723
(2008/02/08)
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- Synthesis of novel substituted diaryl-1,4-diazepines
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In this paper a convenient route to new 2,3-diaryl-substituted 1,4-diazepines is described through cyclization of ethanedione derivatives and 1,3-propanediamine. The ethanedione derivatives required were synthesized by microwave-assisted oxidation from ethanones.
- Ramajayam,Giridhar, Rajani,Yadav
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p. 901 - 906
(2008/02/12)
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- Synthesis and biological evaluation of new phenidone analogues as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors
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A new series of potential human 5-LOX inhibitors structurally related to the 1-phenyl-3-pyrazolidinone (phenidone, 2) has been synthesized and the activity against COX-1, COX-2, and human 5-LOX enzymes has been evaluated. In contrast with literature data, we observed that phenidone resulted to be inactive against human 5-LOX, while retains its activity against cyclooxygenases in a micromolar range. The present results suggest that the substitution of the amino function at the 4-position is detrimental in terms of activity toward COX-1 and COX-2, while the presence of a double bond at the 4,5-position does not alter the biological profile against COX. The absence of activity vs. human 5-LOX strongly suggests a re-consideration of phenidone and its analogs as 5-LOX inhibitors in humans.
- Cusan, Claudia,Spalluto, Giampiero,Prato, Maurizio,Adams, Michael,Bodensieck, Antje,Bauer, Rudolf,Tubaro, Aurelia,Bernardi, Paolo,Da Ros, Tatiana
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- Privileged structure based ligands for melanocortin receptors - Substituted benzylic piperazine derivatives
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Replacement of the aryl piperazine moiety in compound 1 with a variety of substituted benzylic piperazines (6) yields compounds that afford melanocortin receptor 4 (MCR4) activity. Analogs with ortho substitution on the aromatic ring afforded the highest
- Fisher, Matthew J.,Backer, Ryan T.,Collado, Ivan,De Frutos, Oscar,Husain, Saba,Hsiung, Hansen M.,Kuklish, Steve L.,Mateo, Ana I.,Mullaney, Jeffrey T.,Ornstein, Paul L.,Paredes, Cristina Garcia,O'Brian, Thomas P.,Richardson, Timothy I.,Shah, Jikesh,Zgombick, John M.,Briner, Karin
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p. 4973 - 4978
(2007/10/03)
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- Discovery of a potent, selective, and efficacious class of reversible α-ketoheterocycle inhibitors of fatty acid amide hydrolase effective as analgesics
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Fatty acid amide hydrolase (FAAH) degrades neuromodulating fatty acid amides including anandamide (endogenous cannabinoid agonist) and oleamide (sleep-inducing lipid) at their sites of action and is intimately involved in their regulation. Herein we report the discovery of a potent, selective, and efficacious class of reversible FAAH inhibitors that produce analgesia in animal models validating a new therapeutic target for pain intervention. Key to the useful inhibitor discovery was the routine implementation of a proteomics-wide selectivity screen against the serine hydrolase superfamily ensuring selectivity for FAAH coupled with systematic in vivo examinations of candidate inhibitors.
- Boger, Dale L.,Miyauchi, Hiroshi,Du, Wu,Hardouin, Christophe,Fecik, Robert A.,Cheng, Heng,Hwang, Inkyu,Hedrick, Michael P.,Leung, Donmienne,Acevedo, Orlando,Guimar?es, Cristiano R. W.,Jorgensen, William L.,Cravatt, Benjamin F.
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p. 1849 - 1856
(2007/10/03)
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- Esters derived from vanillin and vanillal and aromatic and functionalized aliphatic carboxylic acids
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Reactions of vanillin and vanillal with aromatic and functionally substituted aliphatic carboxylic acid chlorides in the presence of pyridine afforded the corresponding previously unknown esters.
- Dikusar,Kozlov
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p. 992 - 996
(2007/10/03)
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- Synthesis and identification of small molecules that potently induce apoptosis in melanoma cells through G1 cell cycle arrest
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Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenylmethylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 ~ 0.5 μM), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor κ-B (NFκB) in the cell; NFκB is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NFκB and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.
- Dothager, Robin S.,Putt, Karson S.,Allen, Brittany J.,Leslie, Benjamin J.,Nesterenko, Vitaliy,Hergenrother, Paul J.
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p. 8686 - 8696
(2007/10/03)
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- An efficient acid- and metal-free one-pot synthesis of benzothiazoles from carboxylic acids
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Carboxylic acids are converted to benzothiazoles in a one-pot reaction with thionyl chloride followed by treatment with 2-aminothiophenol under acid- and catalyst-free conditions. Georg Thieme Verlag Stuttgart.
- Rudrawar, Santosh,Kondaskar, Atul,Chakraborti, Asit K.
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p. 2521 - 2526
(2007/10/03)
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- Bioactivation of carbamate-based 20(S)-camptothecin prodrugs
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Two new prodrugs of CPT were synthesized, based on carbamate linkages between the 20-hydroxy group of CPT and a linker designed to be enzymatically removed by either Penicillin-G-Amidase or catalytic antibody 38C2. Cell growth inhibition assays showed an
- Pessah, Neta,Reznik, Mika,Shamis, Marina,Yantiri, Ferda,Xin, Hong,Bowdish, Katherine,Shomron, Noam,Ast, Gil,Shabat, Doron
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p. 1859 - 1866
(2007/10/03)
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