- Cavity-extended inherently chiral resorcin[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers
-
Inherently chiral resorcin[4]arenes 2 and 3 were prepared from enantiomerically pure C4-symmetric rccc-2,8,14,20-tetraisobutyl-4,10, 16,22-tetra-O-methylresorcin[4]arene (1). The four 2-bromobenzyl ether residues in precursor 2 were introduced
- Paletta, Marlene,Klaes, Michael,Neumann, Beate,Stammler, Hans-Georg,Grimme, Stefan,Mattay, Jochen
-
-
Read Online
- Stereoinvertive C–C Bond Formation at the Boron-Bound Stereogenic Centers through Copper-Bipyridine-Catalyzed Intramolecular Coupling of α-Aminobenzylboronic Esters
-
Enantiospecific intramolecular Suzuki–Miyaura-type coupling with α-(2-halobenzoylamino)benzylboronic esters to give 3-substituted isoindolinones is achieved by using copper catalysts with 2,2′-bipyridine-based achiral ligands. Enantioenriched α-aminobenzylboron reactants bearing a hydrogen atom at the boron-bound stereogenic carbons undergo stereoinvertive coupling in the presence of a 6-phenyl-2,2′-bipyridine ligand with high enantiospecificity. α-Aminobenzylboronates bearing fully substituted boron-bound stereogenic centers also gave the 3,3-disubstituted isoindolinones with stereospecific stereochemical inversion in the presence of simple 2,2′-bipyridine as a ligand.
- Suginome, Michinori,Yamamoto, Takeshi,Yoshinaga, Yukako
-
supporting information
p. 7251 - 7255
(2020/03/23)
-
- 6-Arylphenanthridines from Aryl o-Biaryl Ketones with 1,1,1,3,3,3-Hexamethyldisilazane and Molecular Iodine
-
Warming treatment of aryl o-biaryl ketones with 1,1,1,3,3,3-hexamethyldisilazane in the presence of Sc(OTf)3 in toluene, followed by the reaction with molecular iodine and K2CO3 in a mixture of THF and methanol at 60 °C gave the corresponding 6-arylphenanthridines in good to moderate yields. The present reaction is a one-pot method for the preparation of 6-arylphenanthridines from aryl o-biaryl ketones through the cyclization of imino-nitrogen-centered radicals that were generated from N-iodo aryl o-biaryl ketimines formed from the reaction of aryl biaryl ketimines with molecular iodine.
- Kobayashi, Eiji,Kishi, Atsushi,Togo, Hideo
-
p. 7335 - 7347
(2019/11/22)
-
- Making endo-cyclizations favorable again: A conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides
-
Although benzotriazoles are important and ubiquitous, currently there is only one conceptual approach to their synthesis: bridging the two ortho-amino groups with an electrophilic nitrogen atom. Herein, we disclose a new practical alternative-the endo-cyclization of 2-azidoaryl lithiums obtained in situ from 2-azido-aryl bromides. The scope of the reaction is illustrated using twenty-four examples with a variety of alkyl, alkoxy, perfluoroalkyl, and halogen substituents. We found that the directing effect of the azide group allows selective metal-halogen exchange in aryl azides containing several bromine atoms. Furthermore, (2-bromophenyl)diazomethane undergoes similar cyclization to give an indazole. Thus, cyclizations of aryl lithiums containing an ortho-X = Y = Z group emerge as a new general approach for the synthesis of aromatic heterocycles. DFT computations suggested that the observed endo-selectivity applies to the anionic cyclizations of other functionalities that undergo "1,1-additions" (i.e., azides, diazo compounds, and isonitriles). In contrast, cyclizations with the heteroatomic functionalities that follow the "1,2-addition" pattern (cyanates, thiocyanates, isocyanates, isothiocyanates, and nitriles) prefer the exo-cyclization path. Hence, such reactions expand the current understanding of stereoelectronic factors in anionic cyclizations.
- Ageshina, Alexandra A.,Chesnokov, Gleb A.,Topchiy, Maxim A.,Alabugin, Igor V.,Nechaev, Mikhail S.,Asachenko, Andrey F.
-
supporting information
p. 4523 - 4534
(2019/05/17)
-
- Method for synthesizing chlorantraniliprole derivative intermediate
-
The invention provides a method for synthesizing a chlorantraniliprole derivative intermediate, belonging to the field of agricultural pesticides. The method comprises the following steps: subjectingthe intermediate 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid to chlorination so as to prepare 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-formyl chloride; subjecting the raw material 2-bromobenzoic acid to acylating chlorination and ammoniation so as to prepare substituted 2-bromo-benzamide; and subjecting 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-formyl chloride and substituted 2-bromo-benzamide to cyclization so as to obtain the chlorantraniliprole derivative intermediate. The method of the invention is simple and common; reagents used in the process of synthesis are low in toxicity, used solvents are recyclable, and few by-products are produced, so the method has little corrosion to equipment and low pollution to environment; since raw materials are cheap, production cost is reduced and good economical efficiency is obtained; therefore, the method has good application prospects.
- -
-
Paragraph 0014; 0015
(2018/04/02)
-
- The Conversion of tert-Butyl Esters to Acid Chlorides Using Thionyl Chloride
-
The reaction of tert-butyl esters with SOCl2 at room temperature provides acid chlorides in unpurified yields of 89% or greater. Benzyl, methyl, ethyl, and isopropyl esters are essentially unreactive under these conditions, allowing for the selective conversion of tert-butyl esters to acid chlorides in the presence of other esters.
- Greenberg, Jacob A.,Sammakia, Tarek
-
p. 3245 - 3251
(2017/03/23)
-
- Design, synthesis and antibacterial activity of isatin derivatives as FtsZ inhibitors
-
Seven isatin derivatives have been designed, and their chemical structures were characterized by single crystal X-ray diffraction studies, 1H NMR, MS, and elemental analysis. Structural stabilization followed by intramolecular as well as intermolecular H-bonds makes these molecules as perfect examples in molecular recognition with self-complementary donor and acceptor units within a single molecule. These compounds were evaluated for antimicrobial activities. Docking simulations have been performed to position compounds into the FtsZ active site to determine their probable binding models. All of the compounds exhibited better antibacterial activities. Interestingly, compound 5c and 5d exhibited better antibacterial activities with IC50 values of 0.03 and 0.05 μmol/mL against Staphylococcus aureus, respectively. Compound 5g displays antibacterial activity with IC50 values of 0.672 and 0.830 μmol/mL against Escherichia coli and Pseudomonas aeruginosa, respectively.
- Lian, Zhi-Min,Sun, Juan,Zhu, Hai-Liang
-
-
- Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones
-
Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an alternative route to functionalized isoquinolines.
- Wu, Youzhi,Sun, Peng,Zhang, Kaifan,Yang, Tie,Yao, Hequan,Lin, Aijun
-
p. 2166 - 2173
(2016/03/15)
-
- Unprecedented Formation of π-Copper Complexes during Sonogashira Coupling: Synthesis of a Unique, Recyclable, Ethynyl Ferrocene Derived Cu(I) Specific Ligand
-
During the synthesis of a chiral oxazolinyl-derived ethynyl ferrocene {Fc-C≡C-C6H4-o-(4-iPr-2-Ox)} (Fc = ferrocenyl; Ox = oxazolinyl), we observed an unprecedented formation of highly air stable and monomeric π-copper(I) complexes 4a and 4b, which were structurally characterized. CuI was used as a cocatalyst in this Sonogashira coupling. By the reaction of 4a with aqueous NH3/DMF, the CuI was removed from the complex and the metal-free compound 5a was obtained. This was found to be an excellent ligand for selectively binding Cu(I) halides. Analogous 4-Ph-substituted oxazoline-based ligand 5b and its Cu-I complex 4c were also isolated and characterized. The possible role of these complexes in explaining the copper cycle proposed for Sonogashira coupling has also been discussed.
- Deb, Mayukh,Kumar, Dheeraj,Singh, Jatinder,Elias, Anil J.
-
p. 1086 - 1091
(2016/06/01)
-
- Magnetically recyclable copper modified GO/Fe3O4 catalyst for efficient synthesis of quinazolinones
-
A series of bioactive quinazolinones were effectively synthesized by the condensation of halide benzamide with amino acid using magnetically recyclable GO/Fe3O4-CuI as catalyst. Magnetic GO/Fe3O4-CuI was prepared via a simple chemical method and characterized by FTIR, powder XRD, and SEM. This heterogeneous copper catalyst can be easily separated from reaction mixtures by an external permanent magnet and reused without any obvious loss in activity which shows its applicability as a reusable and promising catalyst for quinazolinones synthesis.
- Kong, Lu-Lu,Fan, Li-Yan
-
supporting information
p. 827 - 831
(2016/06/14)
-
- Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide
-
To find a new lead compound with high biological activity, a series of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide were designed using linking active substructures method. The target compounds were synthesized from substituted benzoic acid by four steps and their structures were confirmed by 1H NMR, IR spectrum and elemental analysis. The in vitro bioassay results indicated that some target compounds exhibited excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa Mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against S. sclerotiorum with the EC50 value of 29.52 mg/L.
- Lei, Peng,Xu, Yan,Du, Juan,Yang, Xin-Ling,Yuan, Hui-Zhu,Xu, Gao-Fei,Ling, Yun
-
supporting information
p. 2544 - 2546
(2016/07/07)
-
- 2,4-DIOXO-QUINAZOLINE-6-SULFONAMIDE DERIVATIVES AS INHIBITORS OF PARG
-
The present invention relates to compounds of formula I that function as inhibitors of PARG (Poly ADP-ribose glycohydrolase) enzyme activity wherein R1a, R1b, R1c, R1d, R1e, W, X1, X2, X3, X4, X5, X6, X7, c are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions in which PARG activity is implicated.
- -
-
Page/Page column 99; 179
(2016/07/05)
-
- Microwave assisted synthesis of phenanthridinones and dihydrophenanthridines by vasicine/KO: T Bu promoted intramolecular C-H arylation
-
A simple, efficient, rapid and transition metal-free methodology has been developed by utilizing vasicine (a natural product), as a catalyst for the synthesis of phenanthridinones and dihydrophenanthridines. The reaction proceeds through intramolecular C-H arylation with aryl halides in the presence of KOtBu as a base under microwave irradiation in sulfolane as a solvent. The reaction proceeds well with various aryl iodides, bromides and more remarkably with less reactive aryl chlorides for 15 minutes, providing the corresponding products in 45-90% yields.
- Sharma, Sushila,Kumar, Manoranjan,Sharma, Shruti,Nayal, Onkar S.,Kumar, Neeraj,Singh, Bikram,Sharma, Upendra
-
p. 8536 - 8544
(2016/09/28)
-
- Preparation method of 1-alkyl-2-phenyl-4-quinolones
-
Provided is a novel method for synthesizing 1-alkyl-2-phenyl-4-quinolones from 2-halobenzoates. The synthesizing method in the present invention has advantages capable of synthesizing 1-alkyl-2-phenyl-4-quinolones in high yield through a simplified stage in a simple reaction condition by means of 2-halobenzoates as an inexpensive starting material.COPYRIGHT KIPO 2015
- -
-
Paragraph 0023-0026
(2016/10/17)
-
- Palladium catalyzed Csp2-H activation for direct aryl hydroxylation: The unprecedented role of 1,4-dioxane as a source of hydroxyl radicals
-
A novel strategy for direct aryl hydroxylation via Pd-catalysed Csp2-H activation through an unprecedented hydroxyl radical transfer from 1,4-dioxane, used as a solvent, is reported with bio relevant and sterically hindered heterocycles and various acyclic functionalities as versatile directing groups.
- Seth, Kapileswar,Nautiyal, Manesh,Purohit, Priyank,Parikh, Naisargee,Chakraborti, Asit K.
-
supporting information
p. 191 - 194
(2015/01/09)
-
- A further decrease in the catalyst loading for the palladium-catalyzed direct intramolecular arylation of amides and sulfonamides
-
The direct arylation of N-substituted o-bromobenzanilides and benzenesulfonamides via C-H bond functionalization has been developed using very low catalyst loadings. This novel cost-effective and more sustainable method relies on a PCN-type palladium pincer complex as a highly active palladium source, providing a general and efficient access to phenanthridinones, biaryl sultams and related heterocyclic systems. The beneficial effect of water as cosolvent has been observed in this process, which is not seriously influenced by electronic effects at the arene moieties or sterically demanding substituents at the amide or sulfonamide nitrogen. In addition, a number of experiments (kinetic plot, poisoning assays, TEM, ESI) have been performed in order to understand the role of the employed palladium complex in this reaction.
- Conde, Nerea,Churruca, Fátima,Sanmartin, Raul,Herrero, María Teresa,Domínguez, Esther
-
supporting information
p. 1525 - 1531
(2015/05/26)
-
- Regioselective synthesis of 1-substituted indazole-3-carboxylic acids
-
In this article, we study the synthesis of 1-substituted indazole-3-carboxylic acids from 2-halobenzoic acids.
- Veerareddy, Arava,Gogireddy, Surendrareddy,Dubey
-
p. 1311 - 1321
(2015/04/27)
-
- Synthesis, biological evaluation, and molecular docking studies of novel 1-benzene acyl-2-(1-methylindol-3-yl)-benzimidazole derivatives as potential tubulin polymerization inhibitors
-
A series of 1-benzene acyl-2-(1-methylindol-3-yl)-benzimidazole derivatives were designed, synthesized and evaluated as potential tubulin polymerization inhibitors and for the cytotoxicity against anthropic cancer cell lines. Among the novel compounds, compound 11f was demonstrated the most potent tubulin polymerization inhibitory activity (IC50 = 1.5 μM) and antiproliferative activity against A549, HepG2 and MCF-7 (GI50 = 2.4, 3.8 and 5.1 μM, respectively), which was compared with the positive control colchicine and CA-4. We also evaluated that compound 11f could effectively induce apoptosis of A549 associated with G2/M phase cell cycle arrest. Docking simulation and 3D-QSAR model in these studies provided more information that could be applied to design new molecules with more potent tubulin inhibitory activity.
- Wang, Yan-Ting,Qin, Ya-Juan,Yang, Na,Zhang, Ya-Liang,Liu, Chang-Hong,Zhu, Hai-Liang
-
p. 125 - 137
(2015/06/22)
-
- Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination
-
We report the development of a tertiary amine-containing β-turn peptide that catalyzes the atroposelective bromination of pharmaceutically relevant 3-arylquinazolin-4(3H)-ones (quinazolinones) with high levels of enantioinduction over a broad substrate scope. The structure of the free catalyst and the peptide-substrate complex were explored using X-ray crystallography and 2D-NOESY experiments. Quinazolinone rotational barriers about the chiral anilide axis were also studied using density functional theory calculations and are discussed in light of the high enantioselectivities observed. Mechanistic studies also suggest that the initial bromination event is stereodetermining, and the major monobromide intermediate is an atropisomerically stable, mono-ortho-substituted isomer. The observation of stereoisomerically stable monobromides stimulated the conversion of the tribromide products to other atropisomerically defined products of interest. For example, (1) a dehalogenation Suzuki-Miyaura cross-coupling sequence delivers ortho-arylated derivatives, and (2) a regioselective Buchwald-Hartwig amination procedure installs para-amine functionality. Stereochemical information was retained during these subsequent transformations.
- Diener, Matthew E.,Metrano, Anthony J.,Kusano, Shuhei,Miller, Scott J.
-
supporting information
p. 12369 - 12377
(2015/10/12)
-
- Synthesis, characterization and biological evaluation of N-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)benzamides
-
We report the synthesis of a series of different substituted N-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)benzamides by making use of a non-steroidal anti-inflammatory drug known as 4-aminophenazone also called as antipyrine, a compound of great interest in drug chemistry. These compounds possess potential biological applications and were screened against human recombinant alkaline phosphatase including human tissue-nonspecific alkaline phosphatase (h-TNAP), tissue specific human intestinal alkaline phosphatase (h-IAP), human placental alkaline phosphatase (h-PLAP) and human germ cell alkaline phosphatase (h-GCAP). These compounds were also tested for their inhibitory potential against recombinant human and rat ecto-5′-nucleotidases (h-e5-NT & r-e5-NT, respectively). All benzamide derivatives inhibited APs to a lesser degree than e5-NT. The reported compounds are of considerable interest for further applications in the field of medicinal chemistry as these compounds have potential to bind nucleotide protein targets.
- Saeed, Aamer,Ejaz, Syeda Abida,Khurshid, Asma,Hassan, Sidra,Al-Rashida, Mariya,Latif, Muhammad,Lecka, Joanna,Sévigny, Jean,Iqbal, Jamshed
-
p. 86428 - 86439
(2015/11/03)
-
- Design, synthesis, molecular docking studies and in vitro screening of ethyl 4-(3-benzoylthioureido) benzoates as urease inhibitors
-
Thioureas are exceptionally versatile building blocks towards the synthesis of wide variety of heterocyclic systems, which also possess extensive range of pharmacological activities. The substituted benzoic acids were converted into corresponding acid chlorides, these acid chlorides were then treated with potassium thiocyanate in acetone and then the reaction mixture was refluxed for 1-2 h afford ethyl 4-(3-benzoylthioureido)benzoates thioureas in good yields. All the newly synthesized compounds were evaluated for their urease inhibitory activities and were found to be potent inhibitors of urease enzyme. Compounds 1f and 1g were identified as the most potent urease inhibitors (IC50 0.21 and 0.13 μM, respectively), and was 100-fold more potent than the standard inhibitors. Further molecular docking studies were carried out using the crystal structure of urease to find out the binding mode of the inhibitors with the enzyme.
- Saeed, Aamer,Khan, Muhammad Siraj,Rafique, Hummera,Shahid, Mohammad,Iqbal, Jamshed
-
-
- Synthesis and evaluation of novel azoles as potent antifungal agents
-
Using a rational approach to the design of antifungal agents, a series of azole agents with 1,3,4-oxadiazole side chains were designed and synthesized. The results of preliminary in vitro antifungal tests with eight human pathogenic compounds showed that all of the title compounds exhibited excellent activities against all of the tested fungi except Aspergillus fumigatus. Compounds 11e and 11f were found to be the most effective, with a minimum inhibitory concentration of 0.0039 μg/mL, followed by voriconazole, which has a MIC of 0.0625 μg/mL. The 1,3,4-oxadiazole side chain is not the major contributor but plays a role in eliciting the observed antifungal activity.
- Li, Liangjing,Ding, Hao,Wang, Baogang,Yu, Shichong,Zou, Yan,Chai, Xiaoyun,Wu, Qiuye
-
supporting information
p. 192 - 194
(2014/01/17)
-
- A complementary synthetic approach to fluorazone
-
Pyrrole undergoes a regioselective zinc-mediated acylation with 2-bromobenzoyl chloride followed by a Cu-catalyzed N-arylation under microwave irradiation, delivering the important heteroaromatic of fluorazone.
- Calvert, Matthew B.,Sperry, Jonathan
-
p. 282 - 284
(2014/02/14)
-
- Palladium-catalyzed intramolecular asymmetric C-H functionalization/ cyclization reaction of metallocenes: An efficient approach toward the synthesis of planar chiral metallocene compounds
-
A palladium-catalyzed asymmetric synthesis of planar chiral metallocene compounds is reported. The reaction stereoselectively functionalized one of the ortho C-H bonds of Cp rings by intramolecular cyclization to form indenone derivatives in high yields w
- Deng, Ruixian,Huang, Yunze,Ma, Xinna,Li, Gencheng,Zhu, Rui,Wang, Bin,Kang, Yan-Biao,Gu, Zhenhua
-
supporting information
p. 4472 - 4475
(2014/04/17)
-
- Cooperative catalysis by palladium-nickel binary nanocluster for suzuki-miyaura reaction of ortho-heterocycle-tethered sterically hindered aryl bromides
-
The palladium-nickel binary nanocluster is reported as a new catalyst system for Suzuki-Miyaura cross-coupling of ortho-heterocycle-tethered sterically hindered aryl bromides. The inferior results obtained with the reported Pd/Ni salts/complexes or individual Pd/Ni nanoparticles as catalyst reveal the cooperative catalytic effect of the Pd and Ni nanoparticles in the Pd-Ni nanocluster. The broad substrate scope with respect to variation of the 2-arylbenzoxazole moiety and boronic acids, which offers a means for diversity generation and catalyst recyclability, marks a distinct advantage.
- Seth, Kapileswar,Purohit, Priyank,Chakraborti, Asit K.
-
supporting information
p. 2334 - 2337
(2014/05/20)
-
- 2,5-Bis(2-(diphenylphosphino)phenyl)-1,3,4-oxadiazole ligands and their Cu(I) complexes for Sonogashira coupling reaction
-
Two diphosphane ligands - 2,5-bis(2-(diphenylphosphino)-5-R)phenyl)-1,3,4- oxadiazole (L1, R = H, L2, R = OMe) and their binuclear complexes, L1Cu and L2Cu, were prepared and characterized. The molecular structures of L1Cu and L2Cu, as perchlorate salts,
- Lin, Cai-Xia,Zhu, Jia-Fang,Li, Qing-Shan,Ao, Li-Hua,Jin, Yan-Juan,Xu, Feng-Bo,Hu, Fang-Zhong,Yuan, Yao-Feng
-
p. 298 - 303
(2014/04/03)
-
- Enantioselective synthesis of planar chiral ferrocenes via Pd(0)-catalyzed intramolecular direct C-H bond arylation
-
A highly efficient synthesis of planar chiral ferrocenes by enantioselective Pd(0)-catalyzed direct C-H arylation from readily available starting materials under mild reaction conditions was developed (up to 99% yield, 99% ee). The products can be easily transformed to the highly efficient planar ferrocene ligands, which have demonstrated high efficiency in Pd-catalyzed asymmetric allylic alkylation and amination reactions.
- Gao, De-Wei,Yin, Qin,Gu, Qing,You, Shu-Li
-
supporting information
p. 4841 - 4844
(2014/04/17)
-
- Bidentate cycloimidate palladium complexes with aliphatic and aromatic anagostic bonds
-
Palladium(ii) complexes of bidentate cycloimidate ligand systems with a triarylmethyl moiety exhibit exceptional downfield shifts in proton NMR spectra due to rare anagostic interactions. This journal is the Partner Organisations 2014.
- Sch?ler, Stephan,Wahl, Maike H.,Wurster, Nicole I. C.,Puls, Arik,H?ttig, Christof,Dyker, Gerald
-
supporting information
p. 5909 - 5911
(2014/05/20)
-
- 2-(2-Arylphenyl)benzoxazole as a novel anti-inflammatory scaffold: Synthesis and biological evaluation
-
The 2-(2-arylphenyl)benzoxazole moiety has been found to be a new and selective ligand for the enzyme cyclooxygenase-2 (COX-2). The 2-(2-arylphenyl)benzoxazoles 3a-m have been synthesized by Suzuki reaction of 2-(2-bromophenyl)benzoxazole. Further synthetic manipulation of 3f and 3i led to 3o and 3n, respectively. The compounds 3g, 3n, and 3o selectively inhibited COX-2 with selectivity index of 3n much better than that of the COX-2 selective NSAID celecoxib. The in vivo anti-inflammatory potency of 3g and 3n is comparable to that of celecoxib and the nonselective NSAID diclofenac at two different doses, and 3o showed better potency compared to these clinically used NSAIDs.
- Seth, Kapileswar,Garg, Sanjeev K.,Kumar, Raj,Purohit, Priyank,Meena, Vachan S.,Goyal, Rohit,Banerjee, Uttam C.,Chakraborti, Asit K.
-
supporting information
p. 512 - 516
(2014/06/09)
-
- Novel N-acyl/aroyl-2-(5-phenyl-2H-tetrazol-2-yl)acetohydrazides: Synthesis and characterization
-
A number of novel N -acyl/aroyl-2-(5-phenyl-2H-tetrazol-2-yl) acetohydrazides (4a-j) of biological interest were efficiently synthesized by treating 2-(5-phenyl-2H-tetrazole-2-yl)acetohydrazide (3) with a variety of aroyl/heterocyclyl or alkanoyl chlorides. FTIR, 1H NMR, 13C NMR, GC-MS, and elemental analyses data confirmed the structures assigned to the newly synthesized compounds. TUeBITAK.
- Saeed, Aamer,Hussain, Majid,Qasim, Muhammad
-
p. 436 - 442
(2014/06/09)
-
- Synthesis of isoquinolinone-based tricycles as novel poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors
-
The isoquinolinone-based tricyclic compounds were designed and synthesized. Preliminary biological study of these compounds provided potent compounds 17a, 33b, 33c, 33d, and 33g with low nanomolar IC50s against PARP-1 enzyme.
- Chen, Jianyang,Peng, Haixia,He, Jinxue,Huan, Xiajuan,Miao, Zehong,Yang, Chunhao
-
p. 2669 - 2673
(2014/06/09)
-
- Discovery of potent cytotoxic ortho-aryl chalcones as new scaffold targeting tubulin and mitosis with affinity-based fluorescence
-
A series of new ortho-aryl chalcones have been designed and synthesized. Many of these compounds were found to exhibit significant antiproliferation activity toward a panel of cancer cell lines. Selected compounds show potent cytotoxicity against several drug resistant cell lines including paclitaxel (Taxol) resistant human ovarian carcinoma cells, vincristine resistant human ileocecum carcinoma cells, and doxorubicin resistant human breast carcinoma cells. Further investigation revealed that active analogues could inhibit the microtubule polymerization by binding to colchicine site and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells. Furthermore, affinity-based fluorescence enhancement was observed during the binding of active compounds with tubulin, which greatly facilitated the determination of tubulin binding site of the compounds. Finally, selected compound 26 was found to exhibit obvious in vivo antitumor activity in A549 tumor xenografts model. Our systematic studies implied a new scaffold targeting tubulin and mitosis for novel antitumor drug discovery.
- Zhu, Cuige,Zuo, Yinglin,Wang, Ruimin,Liang, Baoxia,Yue, Xin,Wen, Gesi,Shang, Nana,Huang, Lei,Chen, Yu,Du, Jun,Bu, Xianzhang
-
p. 6364 - 6382
(2014/09/29)
-
- COMPOUNDS AND METHODS FOR INDUCING CHONDROGENESIS
-
Described herein are compounds and compositions for the amelioration of arthritis or joint injuries by inducing mesenchymal stem cells into chondrocytes.
- -
-
Paragraph 0772; 0773
(2014/09/29)
-
- Tailoring buchwald-type phosphines with pyrimidinium betaines as versatile aryl group surrogates
-
A derivatization of dialkylbiarylphosphines consisting in the formal replacement of their distal aryl group by a pyrimidinium betaine is reported. Two achiral representatives of this new class of Buchwald-type phosphines have been successfully synthesized through two strategies. The first one is based on a last stage introduction of the phosphino moiety, and the second one consists in a modular, one-pot, three-step procedure starting from an o-bromoaryl phosphine. The resulting phosphines have been coordinated onto gold(I) and palladium(II) centers and have been employed as supporting ligands in Pd-catalyzed Suzuki-Miyaura cross-coupling of aryl halide substrates.
- Nol-Duchesneau, Ludovik,Lugan, Nol,Lavigne, Guy,Labande, Agns,Csar, Vincent
-
supporting information
p. 5085 - 5088
(2014/12/11)
-
- Diastereoselective palladium-catalyzed arylcyanation/heteroarylcyanation of enantioenriched N -allylcarboxamides
-
A diastereoselective Pd-catalyzed arylcyanation/heteroarylcyanation of chiral N-allylcarboxamides using Zn(CN)2 as the cyanide source is reported. Nitrile-containing dihydroisoquinolinone products are obtained in good to excellent yields with u
- Yoon, Hyung,Petrone, David A.,Lautens, Mark
-
supporting information
p. 6420 - 6423
(2015/02/05)
-
- Facile assembly of two 6-membered fused N-heterocyclic rings: A rapid access to novel small molecules via Cu-mediated reaction
-
A rapid, versatile and one-pot Cu-mediated domino reaction has been developed for facile assembly of two six membered fused N-heterocyclic rings leading to novel small molecules as potential inhibitors of PDE4. The Royal Society of Chemistry.
- Adepu, Raju,Sunke, Rajnikanth,Meda, Chandana L. T.,Rambabu,Krishna, G. Rama,Reddy, C. Malla,Deora, Girdhar Singh,Parsa, Kishore V. L.,Pal, Manojit
-
supporting information
p. 190 - 192
(2013/02/22)
-
- An efficient method for the preparation of hydroxamic acids
-
Reactions of acyl chlorides with hydroxylamine hydrochloride and NaHCO 3 generate the corresponding hydroxamic acid products in ethyl acetate and water at room temperature for 5 min. This is a simple and efficient method to synthesize a wide range of hydroxamic acids from carboxylic acids in excellent yield and high purity after simple post-treatment without chromatographic purification. In this process, the highlights are the simple separation of products and cheaply available reagents.
- Gao, Xi-Ai,Wang, Xian-Xue,Yan, Hao,Li, Jian,Yan, Ru-Long,Huang, Guo-Sheng
-
p. 381 - 385
(2013/05/22)
-
- Transition metal-free one-pot synthesis of 2-substituted 3-carboxy-4-quinolone and chromone derivatives
-
A novel one-pot synthesis of the 2-substituted 3-carboxy-4-quinolone/ chromone derivatives from readily available 3-oxo-3-arylpropanoates and amides/acyl chlorides is reported, without any transition metal aid. The Royal Society of Chemistry 2013.
- Lin, Jian-Ping,Long, Ya-Qiu
-
supporting information
p. 5313 - 5315
(2013/06/27)
-
- Palladium-catalyzed ring-opening of cyclopropyl benzamides: Synthesis of benzo[c]azepine-1-ones via C(sp3)-H functionalization
-
A variety of difficult to obtain benzo[c]azepine-1-ones are synthesized via a novel palladium-catalyzed, silver-promoted intramolecular cyclization of cyclopropyl benzamides. This biologically important class of molecules is prepared in an efficient and high-yielding manner from easily accessible starting materials. Both aryl bromides and iodides are effective substrates for the transformation. Mechanistic studies indicate that the reaction proceeds through a cyclopropyl C(sp3)-H cleavage step, followed by ring-opening, deprotonation, and reductive elimination.
- Ladd, Carolyn L.,Roman, Daniela Sustac,Charette, André B.
-
supporting information
p. 4479 - 4487
(2013/06/26)
-
- Facile synthesis and herbicidal evaluation of 2-Aryl-4H-3, 1-benzoxazin-4-ones
-
The present work deals with the synthesis of 4H-3,1-benzoxazin-4-ones carrying an aryl functional group at position-2. Synthesized compounds tested for herbicidal activity at three different doses (500 μg/mL, 50 μg/mL and 5μg/mL). Most of the compounds exhibited significant herbicidal activity against Lemna aequinocitalis welv. at higher dose (500 μg/mL). Among the tested compounds 2-phenyl-4H-3,1-benzoxazin-4-one (3a) and 2-(3-chlorophenyl)- 4H-3,1-benzoxazin-4- one (3l) completely inhibited the plant growth at 500 and 50 μg/mL concentrations. All the synthetic compounds were characterized by FT-IR, 1H NMR, EI-MS and elemental analysis.
- Hussain, Zaib,Khan, Zulfiqar Ali,Naqvi, Syed Ali Raza,Shahzad, Sohail Anjum,Yar, Muhammad,Hussain, Abdullah Ijaz,Chatha, Shahzad Ali Shahid,Mahmood, Nasir,Khan, Khalid Mohammed
-
p. 449 - 455
(2013/07/27)
-
- Synthesis of new N-[3-(Benzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)-ylidene] substituted benzamides
-
A series of novel N -[3-(2-benzo[d]thiazol-2-yl)-4-methylthiazol-2(3H)- ylidene] substituted benzamides (2a-k) were efficiently synthesized by heterocyclization of the corresponding 1-(benzo[d]thiazol-2-yl)-3-aroylthioureas (1a{k). The cyclization was achieved by the reaction of α-bromoacteone produced in situ using bromine in dry acetone in the presence of triethylamine. TUeBITAK.
- Saeed, Aamer,Rafique, Hummera
-
p. 909 - 916
(2013/12/04)
-
- Direct arylation under catalysis of an oxime-derived palladacycle: Search for a phosphane-free method
-
A phosphane-free method for the direct arylation of benzothiazole by employing oxime-derived palladacycle 1 as a catalyst was developed. The new catalyst system can be used for 2-arylations by using aryl bromides and iodides. In addition, this method is especially suitable for the intramolecular direct coupling of bromo-and iodoamides, as well aschloroamides, to achieve a rapid synthesis of benzo[c]phenanthridine alkaloids. Direct arylation reactions under catalysis of an oxime-derived palladacycle were investigated. This phosphane-free method is applicable for the 2-arylation of benzothiazole and is especially suitable for the intramolecular direct coupling of bromo-and iodoamides, as well as chloroamides, to achieve rapid synthesis of benzo[c]phenanthridine alkaloids. Copyright
- Zhang, Guofu,Zhao, Xiaobao,Yan, Yunbing,Ding, Chengrong
-
supporting information; experimental part
p. 669 - 672
(2012/03/27)
-
- An efficient copper mediated synthetic methodology for benzo[d]isothiazol- 3(2H)-ones and related sulfur-nitrogen heterocycles
-
A copper mediated sulfur-nitrogen coupling reaction for the synthesis of benzo[d]isothiazol-3(2H)-ones and related sulfur-nitrogen heterocycles has been presented, which requires 2-halo-arylamides, sulfur powder, 25-50 mol % of copper iodide/1,10-phenanthroline, and potassium carbonate as base.
- Bhakuni, Bhagat Singh,Balkrishna, Shah Jaimin,Kumar, Amit,Kumar, Sangit
-
supporting information; body text
p. 1354 - 1357
(2012/04/10)
-
- Palladium-catalyzed intramolecular decarboxylative coupling of arene carboxylic acids/esters with aryl bromides
-
Give me a ring? An efficient approach has been developed for the intramolecular decarboxylative coupling of arene carboxylic acids/esters with aryl bromides catalyzed by palladium (see scheme). From a synthetic viewpoint, this method is highly attractive because the catalyst loading is low, the optimized reaction conditions are mild, and the substrate scope is broad. Copyright
- Shen, Zengming,Ni, Zhenjie,Mo, Song,Wang, Jing,Zhu, Yamin
-
supporting information; experimental part
p. 4859 - 4865
(2012/06/04)
-
- The synthesis of phosphine oxide-linked bis(oxazoline) ligands and their application in asymmetric allylic alkylation
-
The phosphine oxide-linked bis(oxazoline) ligands were designed and synthesized in two ways. One is the coupling of Grignard reagent derived from 2-(2-bromophenyl)oxazoline with phenylphosphonic dichloride, another route is the condensation of bis(2-formylphenyl)(phenyl)phosphine oxide with chiral amino alcohols followed by NBS oxidation. These new bis(oxazoline) ligands were applied in Pd-catalyzed asymmetric allylic alkylation reactions and good yields and enantioselectivities were obtained with diphenyl substituted ligand (up to 95% ee).
- Jin, Yu,Du, Da-Ming
-
experimental part
p. 3633 - 3640
(2012/06/18)
-
- A highly efficient copper-catalyzed method for the synthesis of 2-hydroxybenzamides in water
-
An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33-96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides. Georg Thieme Verlag Stuttgart · New York.
- Balkrishna, Shah Jaimin,Kumar, Sangit
-
experimental part
p. 1417 - 1426
(2012/06/30)
-
- Enantioselective synthesis of anti-β-hydroxy-α-amido esters by asymmetric transfer hydrogenation in emulsions
-
Herein, we present two methods for an asymmetric transfer hydrogenation through the dynamic kinetic resolution of α-amido-β-ketoesters. These procedures yield the corresponding anti-β-hydroxy-α-amido esters in good yields and with good diastereo- and enantioselectivities. First, the scope of the reduction of α-amido-β-ketoesters by using triethylammonium formate azeotrope is examined. Then, an emulsion technology with sodium formate is explored, which allows for broader substrate scope, faster reaction times, and lower catalyst loading. Furthermore, these reactions are operationally simple and can be set up in air.
- Seashore-Ludlow, Brinton,Villo, Piret,Somfai, Peter
-
supporting information; experimental part
p. 7219 - 7223
(2012/07/13)
-
- Analogues of fenarimol are potent inhibitors of trypanosoma cruzi and are efficacious in a murine model of chagas disease
-
We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC50s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.
- Keenan, Martine,Abbott, Michael J.,Alexander, Paul W.,Armstrong, Tanya,Best, Wayne M.,Berven, Bradley,Botero, Adriana,Chaplin, Jason H.,Charman, Susan A.,Chatelain, Eric,Von Geldern, Thomas W.,Kerfoot, Maria,Khong, Andrea,Nguyen, Tien,McManus, Joshua D.,Morizzi, Julia,Ryan, Eileen,Scandale, Ivan,Thompson, R. Andrew,Wang, Sen Z.,White, Karen L.
-
supporting information; experimental part
p. 4189 - 4204
(2012/07/27)
-
- Synthesis, antimicrobial evaluation, and QSAR analysis of 2-isopropyl-5-methylcyclohexanol derivatives
-
A series of 2-isopropyl-5-methylcyclohexanol derivatives were synthesized and evaluated for their antibacterial activity against Gram-positive Staphylococcus aureus and Bacillus subtilis and Gram-negative Escherichia coli and in vitro antifungal activity against Candida albicans and Aspergillus niger. The results of antimicrobial activity demonstrated that the compounds 10, 20, and 21 were the most active ones among the synthesized compounds. The QSAR studies revealed the importance of dipole moment (μ), total energy (Te), and topological parameters (κ1 and κ3) in describing the antimicrobial activity of 2-isopropyl-5-methylcyclohexanol derivatives. Springer Science+Business Media, LLC 2011.
- Singh, Manjeet,Kumar, Sunil,Kumar, Ashwani,Kumar, Pradeep,Narasimhan, Balasubramanian
-
experimental part
p. 511 - 522
(2012/08/07)
-
- Intramolecular direct dehydrohalide coupling promoted by KOtBu: Total synthesis of amaryllidaceae alkaloids anhydrolycorinone and oxoassoanine
-
A transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution (HAS) with aryl radicals has been developed in the presence of potassium tert-butoxide and an organic molecule as the catalyst. The methodology has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), and other related structures. Interestingly, the method also works only in the presence of potassium tert-butoxide.
- De, Subhadip,Ghosh, Santanu,Bhunia, Subhajit,Sheikh, Javeed Ahmad,Bisai, Alakesh
-
supporting information
p. 4466 - 4469
(2012/10/29)
-