- Palladium-catalyzed C–P bond activation of aroyl phosphine oxides without the adjacent “anchoring atom”
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A novel palladium-catalyzed decarbonylation of aroyl phosphine oxides to prepare phosphine oxides from carboxylic acids is developed. Without the adjacent “anchoring atom”, the challenging C–P bond activation is achieved in high selectivity. The disclosure of this reaction provides a new example of C–P bond activation and helps to extend the understanding of the property of C–P bond.
- Chen, Xingyu,Liu, Xiaoyan,Zhu, Hong,Wang, Zhiqian
-
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- Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole -Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
-
Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.
- G?bel, Dominik,Rusch, Pascal,Duvinage, Daniel,Stauch, Tim,Bigall, Nadja-C.,Nachtsheim, Boris J.
-
supporting information
p. 14333 - 14355
(2021/10/20)
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- Aziridine-2-carboxylic acid derivatives and its open-ring isomers as a novel PDIA1 inhibitors
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[Figure not available: see fulltext.] Acyl derivatives of aziridine-2-carboxylic acid have been synthesized and tested as PDIA1 inhibitors. Calculations of charge value and distribution in aziridine ring system and some alkylating agents were performed. For the first time was found that acyl derivatives of aziridine-2-carboxylic acid are weak to moderately active PDIA1 inhibitors.
- Leite, Irena,Andrianov, Victor,Zelencova-Gopejenko, Diana,Loza, Einars,Kazhoka-Lapsa, Iveta,Domracheva, Ilona,Stoyak, Marta,Chlopicki, Stefan,Kalvins, Ivars
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p. 1086 - 1106
(2022/01/12)
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- Amide prodrug derivatives as protein kinase inhibitors
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The invention relates to amide prodrug compounds of novel kinase inhibitors. The prodrugs are characterized in that amino of original drugs is subjected to amidation modification, so that bioavailability of the original drugs in vivo is significantly improved. The invention further relates to pharmaceutical composition containing the prodrugs and a method for treating cancer or other cell proliferative abnormal diseases by the prodrugs and the pharmaceutical composition.
- -
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Paragraph 0126; 0150-0153
(2019/02/04)
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- Synthesis and biological evaluation of chemokine receptor ligands with 2-benzazepine scaffold
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Targeting CCR2 and CCR5 receptors is considered as promising concept for the development of novel antiinflammatory drugs. Herein, we present the development of the first probe-dependent positive allosteric modulator (PAM) of CCR5 receptors with a 2-benzazepine scaffold. Compound 14 (2-isobutyl-N-({[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-1-oxo-2,3-dihydro-1H-2-benzazepine-4-carboxamide) activates the CCR5 receptor in a CCL4-dependent manner, but does not compete with [3H]TAK-779 binding at the CCR5. Furthermore, introduction of a p-tolyl moiety at 7-position of the 2-benzazepine scaffold turns the CCR5 PAM 14 into the selective CCR2 receptor antagonist 26b. The structure affinity and activity relationships presented here offer new insights into ligand recognition by CCR2 and CCR5 receptors.
- Thum, Simone,Kokornaczyk, Artur K.,Seki, Tomoaki,De Maria, Monica,Ortiz Zacarias, Natalia V.,de Vries, Henk,Weiss, Christina,Koch, Michael,Schepmann, Dirk,Kitamura, Masato,Tschammer, Nuska,Heitman, Laura H.,Junker, Anna,Wünsch, Bernhard
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p. 401 - 413
(2017/05/04)
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- First total synthesis of isoquinolinone alkaloid marinamide and its methyl ester
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The first total synthesis of isoquinolinone alkaloid marinamide 1 and its methyl ester 2 was described. The key steps involved a regioselective Friedel-Crafts reaction of 1-benzyl-1H-pyrrole to form the intermediate 8.
- Feng, Cheng-Liang,Zhang, Shu-Guang,Chen, Jun-Qing,Cai, Jin,Ji, Min
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p. 767 - 769
(2013/07/26)
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- Total synthesis of a novel isoquinolinone alkaloid marinamide and its methyl ester
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A naturally occurring isoquinolinone alkaloid marinamide and its methyl ester were synthesised from phthalic anhydride over eight steps in 46% and 52% overall yield. The key intermediate methyl 2-(1-benzyl-1H-pyrrole-2-carbonyl) benzoate was synthesised from the acid chloride of mono methyl phthalate and 1-benzyl-1H-pyrrole catalysed by Zinc oxide under solvent-free conditions at room temperature.
- Zhang, Shuguang,Feng, Chengliang,Cai, Jin,Chen, Junqing,Ji, Min
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p. 291 - 293
(2013/07/27)
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- NOVEL IMMUNOMODULATOR AND ANTI-INFLAMMATORY COMPOUNDS
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The present invention provides dihydroorotate dehydrogenase inhibitors, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of diseases or disorders wherein the inhibition of Dihydroorotate dehydrogenase is known to show beneficial effect.
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Page/Page column 32
(2011/11/13)
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- NOVEL IMMUNOMODULATOR AND ANTI INFLAMMATORY COMPOUNDS
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The present invention provides dihydroorotate dehydrogenase inhibitors of formula (I), methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of diseases or disorders wherein the inhibition of Dihydroorotate dehydrogenase is known to show beneficial effect.
- -
-
Page/Page column 60
(2011/11/30)
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- BENZIMIDAZOLE INHIBITORS OF LEUKOTRIENE PRODUCTION
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The present invention relates to compounds of formula (I) and pharmaceutically acceptable salt thereof, wherein R1-R7 are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, method
- -
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Page/Page column 102
(2011/06/25)
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- Practical and chemoselective reduction of acyl chloride to alcohol by borohydride in aqueous dichloromethane
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A simple methodology for the reduction of acid chlorides to their corresponding alcohols has been developed. Various carboxylic acids were converted to alcohols in excellent yields using NaBH4-K2CO3 in a mixed solvent system of dichloromethane and water (1:1) in the presence of a phase-transfer catalyst at low temperature. The importance of the work is its simplicity, selectivity, excellent yield, and very short reaction time. This new reduction condition has proved to be an excellent chemoselective method for a range of acid chlorides in the presence of various functional groups.
- Rajan, Ramya,Badgujar, Sachin,Kaur, Kamaljit,Malpani, Yashwardhan,Kanjilal, Pranab R.
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experimental part
p. 2897 - 2907
(2010/11/18)
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- Synthesis of the phosphonoanalogue of benzo[c]pyroglutamic acid
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Phosphonic analogue 1 of benzo[c]pyroglutamic acid was synthesized by three-step synthesis starting from N-tert-butylphtalimide and triethylphosphite. The acid-catalyzed, oxidative cascade conversion of phosphonate 11 to phthalimide and phosphoric acid diethyl ester was observed. A mechanism for this transformation was proposed. Taylor & Francis Group, LLC.
- Kachkovskyi, Georgiy O.,Kolodiazhnyi, Oleg I.
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experimental part
p. 2441 - 2448
(2011/02/25)
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- A Rh(II)-catalyzed cycloaddition approach toward the synthesis of komaroviquinone
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Using a rhodium(II)-catalyzed cyclization/cycloaddition sequence as the key reaction step, the icetexane core of komaroviquinone was constructed by an intramolecular dipolar-cycloaddition of a carbonyl ylide dipole across a tethered π-bond. The ylide was arrived at by cyclization of a rhodium carbenoid intermediate onto a proximal ester group. Efforts toward the preparation of the required precursor for elaboration to the natural product are discussed.
- Padwa, Albert,Chughtai, Majid J.,Boonsombat, Jutatip,Rashatasakhon, Paitoon
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p. 4758 - 4767
(2008/09/20)
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- HETEROARYL SULFONAMIDES AND CCR2
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Compounds are provided that act as potent antagonists of the CCR2 receptor. Animal testing demonstrates that these compounds are useful for treating inflammation, a hallmark disease for CCR2. The compounds are generally aryl sulfonamide derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR2-mediated diseases, and as controls in assays for the identification of CCR2 antagonists.
- -
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Page/Page column 212
(2008/06/13)
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- Conversions of 2-(2-oxo cyclohexylcarbonyl)benzoic acid derivatives to pyrazolo[5,1-a]isoindole and pyrimidine rings
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Phtalic acid derivative of o-methylcarboxybenzoylchloride readily acylates N(1-cyclohexenyl) morpholine and is likely to acylate other enamines along the classic path to 1,3-diketones. It is a convenient route towards o-(1-(1,3-diketone)) derivatives of b
- Voitenko,Pokholenko,Kondratov,Kovtunenko,Andre,Wolf
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p. 163 - 177
(2007/10/03)
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- Efficient construction of the oxatricyclo[6.3.1.00,0]dodecane core of komaroviquinone using a cyclization/cycloaddition cascade of a rhodium carbenoid intermediate
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(Chemical Equation Presented) The rhodium(II)-catalyzed cyclization/cycloaddition cascade of a o-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo[6.3.1.00.0]dodecane substructure of the icetexane diterpene komar
- Padwa, Albert,Boonsombat, Jutatip,Rashatasakhon, Paitoon,Willis, Jerremey
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p. 3725 - 3727
(2007/10/03)
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- A convenient access to thienyl-substituted phthalazines
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A synthesis of 1-alkoxy- and 1-amino- substituted 4-(2-thienyl)- phthalazines is described from halo-derivatives of 4-(2-thienyl)-1-(2H)- phthalazinone 3.
- Raposo, M. Manuela M.,Sampaio, Ana M. B. A.,Kirsch
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p. 1245 - 1251
(2007/10/03)
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- Synthesis of new 1,2,4- and 1,3,4-oxadiazole derivatives
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A novel series of compounds structurally related to non-peptide angiotensin II (AII) receptor antagonists has been prepared. In these compounds, the 'spacer' phenyl ring commonly found in almost all AII receptor antagonists was replaced by 1,2,4- and 1,3,
- Meyer, Emerson,Joussef, Antonio C.,Gallardo, Hugo
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p. 899 - 905
(2007/10/03)
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- Asymmetric protonation of lithium enolate of α-amino acid derivatives using chiral Br?nsted acids
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Chiral alcohols possessing an asymmetric 2-oxazoline ring were synthesized as new chiral Br?nsted acids from tetrahydro-2-furoic acid and (1S, 2R)-2-amino-1,2-diphenylethanol. These alcohols were superior to (S,S)- or (R,R)-imide reported previously as a chiral proton source for enantioselective protonation of lithium enolate of an alanine derivative.
- Yanagisawa,Matsuzaki,Yamamoto
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p. 1855 - 1858
(2007/10/03)
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- The photochemistry of acyl azides; X: Aroylnitrenes for heterocycle synthesis
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Stereoselective cycloaddition of aroylnitrenes, generated by photolysis of the corresponding azides 2a,b with the racemic mixtures of cyclic enol ethers 5b and 5c was achieved with the formation of oxazolines 8. Both the chiral auxiliary attached to the a
- Roeske,Abraham
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p. 1125 - 1132
(2007/10/03)
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- New anti-inflammatory N-pyridinyl(alkyl)phthalimides acting as tumour necrosis factor-α production inhibitors
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This paper describes the synthesis of N-pyridinyl(alkyl)phthalimides related to N-phenyl-4,5,6,7-tetrafluorophthalimides known to be inhibitors of tumour necrosis factor-α (TNFα) production. Pharmacomodulation at the phthalimidic nitrogen led to the selection of two pharmacophoric fragments (2,4-lutidinyl and β-picolyl), allowing significant inhibition of TNFα production (compounds 12 and 17). Variation of the substituents linked to the homocycle of their phthalimide scaffold indicated that high (TNFα production) inhibitory potency could be achieved, notably by 5-fluoro, 4- or 5-nitro, 5-amino and especially tetrafluoro substitution. The most active compound, N-(pyridin-3-ylmethyl)-4,5,6,7-tetrafluorophthalimide (32) (84% inhibition at 10 μM), also produced an anti-oedematous effect in the PMA-induced mouse-ear swelling test. Although less active than dexamethasone, it exerted a marked reduction in ear thickness after oral administration (63% vs. 85% for dexamethasone at 0.2 mM kg-1) and remained efficient after topical application (46% vs. 96% for the dexamethasone). It also induced potent inhibition in the rat carrageenan foot oedema test with an ID50 (0.14 μM kg-1) comparable with that of N-(2,6-diisopropylphenyl)phthalimide (4) (0.15 μM kg-1).
- Collin, Xavier,Robert, Jean-Michel,Wielgosz, Gaetane,Le Baut, Guillaume,Bobin-Dubigeon, Christine,Grimaud, Nicole,Petit, Jean-Yves
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p. 639 - 649
(2007/10/03)
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- Synthetic studies towards the O-specific polysaccharide of Shigella Sonnei
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Synthetic routes are described to zwitter-ionic disaccharides that are diastereoisomerically related to frame-shifted repeating units of the title polysaccharide that contains 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose and 2-acetamido-2-deoxy-L-altrur
- Medgyes, Adel,Bajza, Istvan,Farkas, Erzsebet,Pozsgay, Vince,Liptak, Andras
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p. 285 - 310
(2007/10/03)
-
- Synthesis and potent tumour necrosis factor-α production inhibitory activity of N-pyridinylphthalimides and derivatives
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A series of N-azaaryl(alkyl)phthalimides incorporating amino(alkyl)pyridines were synthesized and tested as inhibitors of TNF-α production. The most potent compounds were N-(4,6-dimethyl-pyridin-2-yl)tetrafluorophthalimide (8, 40% inhibition at 10 μM), N-(3-methylpyridinyl)-5-fluorophthalimide (12, 48%) and N-(3-methylpyridinyl)tetrafluorophthalimide (13, 68%). The analogues without (tetra)fluorine substitution on the aromatic ring were less active inhibitors.
- Collin,Robert,Robert-Piessard,Le Baut,Bobin-Dubigeon,Vernhet,Lang,Petit
-
-
- Syntheses of new chiral 1,2-diamines and δ-amino-alcohols and their application in catalytic enantioselective C-C bond formations at an elevated temperature of up to 110°C
-
The syntheses of new chiral 1,2-diamines 6a-e and chiral δ-amino-alcohols (-)-10a-e, (+)-10d-e and their use as ligands in catalytic asymmetric additions of diethylzinc to benzaldehyde are described. The diamines were found to be efficient catalysts which
- Eilers,Wilken,Martens
-
p. 2343 - 2357
(2007/10/03)
-
- Tyrosine kinase inhibitors. 4. Structure-activity relationships among N- and 3-substituted 2,2'-dithiobis(1H-indoles) for in vitro inhibition of receptor and nonreceptor protein tyrosine kinases
-
A series of 3-substituted 2,2'-dithiobis(1H-indoles) were synthesized and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase, to extend the available structure-activity relationships for this series. The majority of the compounds were prepared either by reaction of 2-chloro-1-methylindole-3-carbonyl chloride with amines, followed by thiomethylation, demethylation, and oxidative dimerization, or by reaction of isocyanates with the anion of 1-methyl-2-indolinethione followed by dimerization. Overall, inhibitory activity is retained by analogues having a wide variety of side chains. A series of 3-carboxamide analogues had moderate to good activity against isolated EGFR (IC50s 1-20 μM), with monoalkyl substitution of the carboxamide being optimal. Polar side chains were generally less effective than lipophilic ones, with benzyl being particularly effective. However, N,N-disubstitution was the most effective pattern for inhibition of pp60(v-src). A variety of substituted N-phenylcarboxamides had lower activity against EGFR than the parent derivative, and a N- thienylcarboxamide also had low activity. A series of 3-ketones, including methyl, phenyl, and furyl derivatives, showed moderate activity against the pp60(v-src) kinase, but were less effective against EGFR. The mechanism of inhibition of both kinases by these drugs was shown to be noncompetitive with respect to both ATP and peptide substrate. Selected compounds inhibited the growth of Swiss 3T3 cells with IC50s in the low micromolar range and inhibited bFGF-mediated intracellular tyrosine phosphorylation in the same cell line. Thiol inhibits the effects of the compounds, suggesting that one possible mechanism of inhibition is thiol-disulfide exchange with thiol- containing residues in the catalytic sites. Crystal structures of two representative compounds show a folded, V-shaped structure, with the disulfide bridge exposed, consistent with this hypothesis.
- Palmer,Rewcastle,Thompson,Boyd,Showalter,Sercel,Fry,Kraker,Denny
-
-
- Reduction of DDHQ and TCC esters by NaBH4 - Its specificity in the presence of alkyl/aryl esters
-
DDHQ/TCC esters 3a-f, 7a-g were prepared either by oxidation of spiroketones 1 with DDQ/o-chloranil or by condensation of acid chloride with DDHQ/TCC. NaBH4 reduction of unsaturated DDHQ 3a-b and TCC 7a-c esters gave the corresponding allylic alcohols in good yield without any observable 1,4-addition products. Reduction of saturated esters 3e,7d, gave the corresponding alcohols. Alkyl esters 5 and 6, methyl benzoate and phenyl benzoate remained unaffected under these reduction conditions. In the reduction of compound 7e containing both alkyl and TCC esters, TCC ester is selectively reduced. Reduction of TCC mono esters 7f-g gave the lactones. The observed facile reduction has been rationalised.
- Kasturi,Pragnacharyulu
-
p. 4431 - 4438
(2007/10/02)
-
- 2-(1-substituted-2-imidazolin-2-yl)benzoic and nicotinic acids and a method for their preparation
-
2-(1-Substituted-2-imidazolin-2-yl)benzoic and nicotinic acids, and derivatives thereof, which are effective in the control of undesirable plant species are described. Also described are a method for the herbicidal use of the compounds and a method for their preparation.
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-
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- Preparation of 13-Substituted 8H-Dibenzoquinolizin-8-ones by Intramolecular Wittig-Horner Reaction of Dialkyl 2-(o-Acylbenzoyl)-1,2-dihydro-1-isoquinolylphosphonates
-
Dialkyl 2-(o-acylbenzoyl)-1,2-dihydro-1-isoquinolyl-phosphonates (1) were prepared by reactions of isoquinoline, o-acylbenzoyl chloride, and trialkyl phosphites.Treatment of 1 with lithium diisopropylamide gave 13-substituted 8H-dibenzoquinolizin-8-ones by intramolecular Wittig-Horner reaction.Especially, 13-alkoxy and dimethylamino derivatives were obtained in good yields.A similar reaction of dimethyl 1--1,2-dihydro-2-quinolylphosphonate was also described.
- Akiba, Kin-ya,Negishi, Yoshio,Inamoto, Naoki
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p. 2188 - 2192
(2007/10/02)
-
- UNE NOUVELLE SYNTHESE DE DERIVES DE L'INDANEDIONE-1,3
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Reaction of Ph3P=CH-COOEt with phthalic anhydride derivatives leads directly, or via the corresponding functional indenone, to 2-alkyl 2-ethoxy- carbonyl 1,3-indanediones according to an original process.
- Babin, P.,Dunogues, J.
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p. 3071 - 3074
(2007/10/02)
-
- ORGANISCHE PHOTOCHEMIE XLIII. Diphenylphosphinigsaeure, Hetero- und Carbocyclen aus ortho-?-funktionalisierten Aroyl-Diphenylphosphinen durch UV-Bestrahlung in Loesung
-
New aroyl diphenyl phosphines (1f-i) substituted with ?-functions in ortho-positions of the aroyl part have been synthesized and photolyzed in benzene.In two cases (1h and i) 1.2- and 1.4-addition products of photochemically formed diphenylphosphinous acid (3) with acetone or phenanthrene quinone (8) are isolated in 59percent yields.Moreover, in neighboring-group participations aroyl radicals formed by competing α-cleavages of 1g-i yield 5- and 6-membered hetero- and carbocycles: xanthone (6), 3,3'-dimethoxy 3,3'-diphthalidyl (7), or the phenanthrene derivative 9, respectively.
- Dankowski, Manfred,Praefcke, Klaus
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p. 131 - 140
(2007/10/02)
-
- Aspects of Tautomerism: Part X - Neighbouring Group Effects on the Structure and Reactivity Patterns of Acid Chlorides
-
The influence of neighbouring groups on the structure and reactivity patterns of over one hundred acid chlorides derived from γ- and δ-keto acids, 1,2- and 1,3-dicarboxylic acid half-esters and diacid chlorides have been examined.Contrary to reports in the literature, text books and monographs, evidence has been obtained for the non-existence of tautomerism between the isomeric pairs of either acid chlorides or half-ester acid chlorides.ce.
- Bhatt, M. Vivekananda,El Ashry, Shaker H.,Somayaji, Vishwanatha
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p. 473 - 486
(2007/10/02)
-