cas 66521-54-8, 3-(DIMETHYLAMINO)-1-(2-PYRIDYL)-2-PROPE&

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Method for large-scale production α, α, α .
The invention discloses a method for large-scale production α, α, α . The reaction operation in Step a was as follows: At room temperature 2 - acetyl pyridine was added. Then N mL of N -dimethyl formamide dimethyl acetal and a catalyst are added to the organic solvent, and after the reaction is completed, the reaction solution is poured into an aqueous sodium hydroxide solution, and then the resulting organic phase is washed, dried, concentrated and recrystallized to obtain an intermediate: 1 - (3 - pyridyl) -3 - (dimethylamino) -2 - propylene -1 - ketone. The method disclosed by the invention is easy to implement large-scale production, high in yield, low in cost, simple to operate and mild in reaction condition.
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Paragraph 0030-0042

(2021/09/08)

Structure-dependent regioselectivity of a roll-over cyclopalladation occuring at 2,2′-bipyridine-type ligands
In this work, different bipyridine-analogue ligands bearing a dimethylamino group in the meta-position of one of the heterocyclic rings were synthesized and reacted with palladium(II) acetate under identical conditions. Cyclometallated palladium(II) complexes with C,N- or C,N,N’-coordinating chelate ligands are formed which were characterized by elemental analysis, 1H and 13C NMR spectroscopy, and single crystal X-ray diffraction analysis. In the case of the mononuclear, C,N,N’-coordinated complex, which is formed by an attack of the palladium(II) site at of the N-methyl groups, the primarily coordinating acetato ligand is exchanged against a chlorido ligand, which is liberated from the solvent dichloromethane by a nucleophilic substitution reaction. In contrast, cyclometallation occurring at one of the six-membered heterocycles leads to dinuclear acetato-bridged palladium(II) complexes.
Becker, Yanik,Sch?n, Florian,Becker, Sabine,Sun, Yu,Thiel, Werner R.
(2021/04/02)

A family of polyoxometalate-resorcin[4]arene-based metal–organic materials: Assemblies, structures and lithium ion battery properties
Polyoxometalates (POMs) are alternative anode materials of lithium ion batteries (LIBs) for their reversible electrochemical redox behaviors and electron storage functions. To overcome the low conductivity and poor stability of the POMs, embedment of POMs into metal–organic hybrid complexes is a promising synthetic strategy. Here, we designed a family of copper-containing POM-resorcin[4]arene-based complexes supported by a resorcin[4]arene ligand (TPTR4A), copper cations and Keggin-type POMs, namely, [Cu4(TPTR4A)2][PMo12O40](OH)·2DMA·H2O (1a), [Cu4(TPTR4A)2][SiW12O40]·2.5DMA (1b) and [Cu4(TPTR4A)2][PW12O40](OH)·0.5DMA·5H2O (1c) (DMA = N,N’-dimethylacetamide). To improve the conductivity of the complexes, composites 1a@GO-1c@GO were obtained through mechanical grinding of the complexes and graphene oxide (GO). Strikingly, they show high initial specific capacity and stability for LIBs. This work offered a strategy for application of the POM-based complexes as LIBs via combining POM-based complexes and RGO.
Yu, Ming-Yue,Liu, Jin-Hua,Yang, Jin,Ma, Jian-Fang
supporting information

(2021/02/26)

Structure-Based Discovery of Pyrimidine Aminobenzene Derivatives as Potent Oral Reversal Agents against P-gp- And BCRP-Mediated Multidrug Resistance
Overexpression of ATP binding cassette (ABC) transporters, including P-glycoprotein (P-gp) and breast cancer resistance protein (BCRP), is an important factor leading to multidrug resistance (MDR) in cancer treatments. Three subclasses of dual inhibitors of P-gp and BCRP were designed based on the active moieties of BCRP inhibitors, tyrosine kinase inhibitors, and P-gp inhibitors, of which compound 21 possessed low cytotoxicity, high reversal potency, and good lipid distribution coefficient. 21 also increased the accumulation of Adriamycin (ADM) and Mitoxantrone (MX), blocked Rh123 efflux, and made no change in the protein expression of P-gp and BCRP. Importantly, coadministration of 21 can significantly improve the oral bioavailability of paclitaxel (PTX). It was also demonstrated that 21 significantly inhibited the growth of K562/A02 xenograft tumors by increasing the sensitivity of ADM in vivo. In summary, 21 has the potential to overcome MDR caused by P-gp and BCRP and to improve the oral bioavailability of PTX.
Qiu, Qianqian,Zou, Feng,Li, Huilan,Shi, Wei,Zhou, Daoguang,Zhang, Ping,Li, Teng,Yin, Ziyu,Cai, Zilong,Jiang, Yuxuan,Huang, Wenlong,Qian, Hai
p. 6179 - 6197
(2021/06/01)

Stereoselective synthesis of trifluoromethyl-substituted 2: H -furan-amines from enaminones
A straightforward strategy for synthesis of highly functionalized trifluoromethyl 2H-furans is described. The copper catalyzed method relies on a cascade cyclic reaction between enaminones and N-tosylhydrazones. This method allows the synthesis of 2-amino
Liang, Xiaoyu,Guo, Pan,Yang, Wenjie,Li, Meng,Jiang, Chengzhou,Sun, Wangbin,Loh, Teck-Peng,Jiang, Yaojia
supporting information
p. 2043 - 2046
(2020/02/22)

Synthesis and biological evaluation of (3/4-(pyrimidin-2-ylamino)benzoyl)-based hydrazine-1-carboxamide/carbothioamide derivatives as novel RXRα antagonists
Abnormal alterations in the expression and biological function of retinoid X receptor alpha (RXRα) have a key role in the development of cancer. Potential modulators of RXRα as anticancer agents are explored in growing numbers of studies. A series of (4/3-(pyrimidin-2-ylamino)benzoyl)hydrazine-1-carboxamide/carbothioamide derivatives are synthesised and evaluated for anticancer activity as RXRα antagonists in this study. Among all synthesised compounds, 6A shows strong antagonist activity (half maximal effective concentration (EC50) = 1.68 ± 0.22 μM), potent anti-proliferative activity against human cancer cell lines HepG2 and A549 cells (50% inhibition of cell viability (IC50) values 50 values > 100 μM). Further bioassays indicate that 6A inhibits 9-cis-RA-induced activity in a dose-dependent manner, and selectively binds to RXRα-=LΒD with submicromolar affinity (Kd = 1.20 × 10?7 M). 6A induces time-and dose-dependent cleavage of poly ADP-ribose polymerase, and significantly stimulates caspase-3 activity, leading to RXRα-dependent apoptosis. Finally, molecular docking studies predict the binding modes for RXRα-LBD and 6A.
Chen, Xiaohui,Fang, Meijuan,Guo, Kaiqiang,Liu, Jie,Liu, Weihao,Qin, Jingbo,Tang, Bowen,Wu, Chunxiao,Wu, Tong,Wu, Zhen,Xu, Jianwen,Zhou, Hu
p. 880 - 896
(2020/04/07)

Synthesis method of 3-formyl indole derivatives
The invention discloses a synthesis method of 3-formyl indole derivatives. The method comprises the following steps: reacting 3-(dimethylamino)-1-(2-pyridyl)-2-propenone with N-substituted aniline ina solvent under the actions of a palladium catalyst and an oxidant, and carrying out after-treatment after the reaction finishes to obtain the 3-formyl indole derivatives. According to the method, a C-H/C-H cross dehydrogenation coupling strategy serves as a key step, seven 3-formyl indole derivatives with potential activity are simply and conveniently synthesized, and raw materials used in the method are cheap, simple and easy to obtain.
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Paragraph 0034-0036

(2020/11/02)

COMPOUNDS AND METHODS FOR HEMATOPOIETIC REGENERATION
The invention relates to compounds that promote hematopoietic regeneration. The invention further relates to methods of promoting hematopoietic regeneration using the novel compounds of the invention.
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Page/Page column 82-83

(2019/06/17)

Design, synthesis, and biological evaluation of triazolyl- and triazinyl-quinazolinediones as potential antitumor agents
Novel 6(3-1H-1,2,4-triazol-1-yl)-3-phenylquinazoline-2,4(1H,3H)-diones (7a-e) were synthesized from different enaminones (6a-e) with 6-hydrazinyl-3-phenylquinazoline-2,4(1H,3H)-dione. 2,6(4-2-Substituted-1,3,5-triazin-1(2H)-yl)-3-phenylquinazoline-2,4(1H,3H)-diones (8a-k) were synthesized from the reaction of 1-(2,4-dioxo-3-phenyl-1,2,3,4-tetrahydroquinazolin-6-yl)thiourea, urea, or guanidine (3a-c) with enaminones (6a-e), and a series from 3-substituted-2-imino-1,3,5-triazin-1(2H)-yl-sulfonyl-phenyl-1-methylquinazoline-2,4(1H,3H)-dione (12a-j) were obtained from the reaction of N-(diaminomethylene)-4-(1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)benzenesulfonamide (11) with the enaminone (6a-j). The antitumor activity of the synthesized compounds was evaluated against two human cell lines: human colon carcinoma HCT116 and human hepatocellular carcinoma HEP-G2. Some of the tested compounds showed significant potency compared to the reference drug staurosporin.
Al-Romaizan, Abeer N.,Ahmed, Nesreen S.,Elfeky, Sherin M.
(2019/03/07)

A Bipyridine-Palladium Derivative as General Pre-Catalyst for Cross-Coupling Reactions in Deep Eutectic Solvents
A versatile and DES-compatible bipyridine palladium complex has been developed as a general pre-catalyst for different cross-coupling reactions (Hiyama, Suzuki-Miyaura, Heck-Mizoroki and Sonogashira) in deep eutectic solvents. Hydrogen bond capacity of the ligand allows to keep the excellent level of results previously obtained in classical organic solvents. Palladium pre-catalyst showed a high catalytic activity for many cross-coupling reactions, demonstrating a great versatility and applicability. Also, this methodology employs sustainable solvents as a reaction medium and highlights the potential of DES as alternative solvents in organometallic catalysis. The catalyst and DES were easily and successfully recycled. The formation of PdNPs in DES has been confirmed by TEM and XPS analysis and their role as catalyst by mercury test. The dynamic coordination of bipyridine-type ligand in the palladium complex formation has been studied via UV/Vis. (Figure presented.).
Saavedra, Beatriz,González-Gallardo, Nerea,Meli, Alessandro,Ramón, Diego J.
supporting information
p. 3868 - 3879
(2019/07/12)

Whole microwave syntheses of pyridylpyrazole and of Re and Ru luminescent pyridylpyrazole complexes
The synthesis of 3-(2pyridyl)pyrazole (pypzH) by conventional methods requires refluxing at high temperatures during more than 16 h, but this is reduced to two consecutive steps of 2 h at 100 °C, and of 10 min at 50 °C in a microwave (MW) assisted synthesis. Its coordination as chelating ligand to the “fac-ReIBr(CO)3” and “RuII(bipy)2” fragments also occurs MW assisted in 5 or 10 min, respectively. A new MW assisted synthetic method is also described for the synthesis of the starting material [Ru(bipy)2Cl2]·2H2O. Both pypzH complexes are characterized by X-ray crystallography, and the study of their photophysical properties support their phosphorescence. The electrochemistry of the Ru complex indicates that electrochemical oxidation is followed by a chemical process.
Merillas, Beatriz,Cuéllar, Elena,Diez-Varga, Alberto,Asensio-Bartolomé, Miryam,García-Herbosa, Gabriel,Torroba, Tomás,Martín-Alvarez, Jose M.,Miguel, Daniel,Villafa?e, Fernando
p. 1 - 7
(2018/09/18)

Excited-State Kinetics of an Air-Stable Cyclometalated Iron(II) Complex
The complex class [Fe(N^N^C)(N^N^N)]+ with an Earth-abundant metal ion has been repeatedly suggested as a chromophore and potential photosensitizer on the basis of quantum chemical calculations. Synthesis and photophysical properties of the parent complex [Fe(pbpy)(tpy)]+ (Hpbpy=6-phenyl-2,2′-bipyridine and tpy=2,2′:6′,2′′-terpyridine) of this new chromophore class are now reported. Ground-state characterization by X-ray diffraction, electrochemistry, spectroelectrochemistry, UV/Vis, and X-ray spectroscopy in combination with DFT calculations proves the high impact of the cyclometalating ligand on the electronic structure. The photophysical properties are significantly improved compared to the prototypical [Fe(tpy)2]2+ complex. In particular, the metal-to-ligand absorption extends into the near-IR and the 3MLCT lifetime increases by 5.5, whereas the metal-centered excited triplet state is very short-lived.
Steube, Jakob,Burkhardt, Lukas,P?pcke, Ayla,Moll, Johannes,Zimmer, Peter,Schoch, Roland,W?lper, Christoph,Heinze, Katja,Lochbrunner, Stefan,Bauer, Matthias
supporting information
p. 11826 - 11830
(2019/07/04)

A catalyst-free four-component domino reaction for the synthesis of functionalized 3-acyl-1,5-benzodiazepines
Various functional 3-acyl-1,5-benzodiazepines containing carboxyl, ester and acyl groups at the 2-position were synthesized via an efficient, sustainable and catalyst-free domino reaction. During the synthesis process, one new cycle and four new bonds (on
Sun, Yue-Wei,Bei, Yue-Ming,Wang, Lan-Zhi
p. 930 - 938
(2019/01/30)

[3+2] Anionic Cycloaddition of Isocyanides to Acyclic Enamines and Enaminones: A New, Simple, and Convenient Method for the Synthesis of 2,4-Disubstituted Pyrroles
We herein demonstrate a new approach for the synthesis of 2,4-disubstituted pyrroles by [3+2] cycloaddition reaction of isocyanides to the activated double bond of various enamines and enaminones. This process paved the way for the synthesis a series of 2,4-disubstituted pyrroles, which are known to be intermediates in the synthesis of biologically active compounds, in good to excellent yields from simple and commercially available starting materials. The process is carried out efficiently using a strong base, tBuOK, at low temperatures (0 °C). The described method is simple, proceeds in one step, does not require additional catalysts and hence, has a wide scope.
Bakulev, Vasiliy A.,Efimov, Ilya V.,Luque, Rafael,Matveeva, Maria D.,Voskressensky, Leonid G.
supporting information

(2020/02/27)

Highly Site-Selective Metal-Free C-H Acyloxylation of Stable Enamines
A highly site-selective acyloxylation of stable enamines with PhI(OAc)2 under metal-free conditions to afford (E)-vinyl acetate derivatives in good to excellent yields is described. Depending on the judicious choice of the solvent system, either the α- or β-site-selective product could be obtained with high selectivity. For the α-site-selective product, the rearranged amide compound is obtained as the major product. This reaction proceeds under mild reaction conditions (room temperature, metal-free, and open-flask) and features a broad substrate scope.
Wang, Fei,Sun, Wangbing,Wang, Yixin,Jiang, Yaojia,Loh, Teck-Peng
supporting information
p. 1256 - 1260
(2018/02/23)

SUBSTITUTED DIHYDROINDENE-4-CARBOXAMIDES AND ANALOGS THEREOF, AND METHODS USING SAME
The present invention includes novel substituted bicyclic compounds, and compositions comprising the same, that can be used to treat or prevent hepatitis B virus (HBV) infections in a patient. In certain embodiments, the compounds and compositions of the invention are capsid inhibitors. (Formula I)
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Page/Page column 204; 206

(2018/10/19)

Organometallic compound, organic light-emitting device, and lighting device employing the same
Organometallic compounds, organic light-emitting devices, and lighting devices employing the same are provided. The organometallic compound has a chemical structure represented by formula (I) or (II): wherein n is 1 or 2; each R1 is independent and can be hydrogen, C1-8 alkyl, C1-8 alkoxy, C5-10 aryl, or C2-8 heteroaryl; each R2 is independent and can be hydrogen, C1-8 fluoroalkyl, or C1-8 alkyl; A is N, or CH; B is N, or CH; D is N, or C—R3, wherein R3 is H, or C1-8 alkyl; and R1 is not hydrogen when R2 is hydrogen.
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Page/Page column 17-18

(2018/02/28)

Design and synthesis of novel benzenesulfonamide containing 1,2,3-triazoles as potent human carbonic anhydrase isoforms I, II, IV and IX inhibitors
In a quest to discover new biologically active compounds, a series of twenty novel heterocyclic derivatives substituted at position 5 with -H (7a-7j) or -CF3 (8a-8j), bearing benzenesulfonamide at N-1 position and various aroyl groups at position 4 of the 1,2,3-triazole ring was synthesized and screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibition potential against four human (h) isoforms hCA I, II, IV and IX. All the compounds (7a-7j and 8a-8j) were synthesized via [3+2] cycloaddition reaction from 4-azidobenzenesulfonamide. Interestingly, compounds 7a-7j were prepared in one pot manner via enaminone intermediate using novel methodology. All the newly synthesized compounds (7a-7j & 8a-8j) were found to be excellent inhibitors of edema related isoform hCA I with their inhibition constant (Ki) ranging from 30.1 to 86.8 nM as compared to standard drug acetazolamide (AAZ) with Ki = 250 nM. Further it was found that most of tested compounds were weaker inhibitors of isoform, hCA II although compounds 7b, 7d-7e, 8a, 8d-8f, 8i (mostly with electron withdrawing substituents) have shown better inhibition potential (Ki i = 52.4 nM) than AAZ (Ki = 74 nM) while against tumor associated hCA IX, all the compounds have shown moderate inhibition potential. Present study have added one more step in exploring the 1,2,3-triazlole moiety in the medicinal field.
Kumar, Rajiv,Vats, Lalit,Bua, Silvia,Supuran, Claudiu T.,Sharma, Pawan K.
p. 545 - 551
(2018/06/18)

Preparation method for terpyridine pyridinium complex and application thereof in reverse transcriptase inhibition
The invention belongs to the field of research and development of HIV inhibitors, and discloses a preparation method for a terpyridine pyridinium (II) complex and application thereof in HIV reverse transcriptase inhibition. The structure of a cationic moiety of the terpyridine pyridinium (II) complex is as shown in a formula I. A preparation process for the terpyridine pyridinium (II) complex is optimized, the raw material cost is low, and the reaction time is short. The obtained complex is high in purity and yield and has good water solubility and excellent spectral properties. The terpyridine pyridinium (II) complex has the capability of selective binding to a TAR region on HIV RNA, and can block the reverse transcription process of viral RNA by reverse transcriptase and inhibit the replication of viral RNA. The terpyridine pyridinium (II) complex is a highly affinitive HIV RNA selective binding reagent and a highly active HIV reverse transcriptase inhibitor, and is an HIV drug having a great application potential.
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Paragraph 0022; 0023

(2019/01/16)

Directed C-C bond cleavage of a cyclopropane intermediate generated from: N -tosylhydrazones and stable enaminones: Expedient synthesis of functionalized 1,4-ketoaldehydes
An efficient method to construct functionalized 1,4-ketoaldehydes bearing all-carbon α-quaternary centers via regioselective C-C bond activation has been described. The cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from
Ni, Meiyan,Zhang, Jianguo,Liang, Xiaoyu,Jiang, Yaojia,Loh, Teck-Peng
supporting information
p. 12286 - 12289
(2017/11/20)

The compound of the structural unit containing pyrazole
The invention discloses a compound containing a pyrazole structural unit. A structural general formula of the compound is shown as a formula I. Because that an electrophosphorescent material requires good film-forming performance and a high-efficiency phosphorescence material having short phosphorescence life, by aiming at enhancement of luminescence efficiency and luminescent device performance, the invention provides a series of electrophosphorescent materials of iridium or platinum complex having pyrazole group. The compound has excellent film forming ability and high luminescence efficiency, the raw material is easily available, the compound is simple to prepare, the total yield is high, the cost of phosphorescence material is greatly reduced, and the compound has important application value.
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Paragraph 0093; 0094; 0095

(2017/08/25)

Selective Extraction of Americium(III) over Europium(III) Ions with Pyridylpyrazole Ligands: Structure–Property Relationships
To clarify the structure–property relationships of pyridylpyrazole ligands and provide guidance for the design of new and more efficient ligands for the selective extraction of actinides over lanthanides, a series of alkyl-substituted pyridylpyrazole ligands with different branched chains at different positions of the pyrazole ring were synthesized. Extraction experiments showed that the pyridylpyrazole ligands exhibited good selective extraction abilities for AmIIIions, and the steric effects of the branched chain had a significant impact on the distribution ratios of AmIIIand EuIIIions as well as the separation factor. Moreover, both slope analyses and UV/Vis spectrometry titrations indicated the formation of a 1:1 complex of 2-(1-octyl-1H-pyrazol-3-yl)pyridine (C8-PypzH) with EuIIIions. The stability constant (log K) for this complex obtained from the UV/Vis titration was 4.45 ± 0.04. Single crystals of the complexes of 3-(2-pyridyl)pyrazole (PypzH) with Eu(NO3)3and Sm(NO3)3were obtained; PypzH acts as a bidentate ligand in the crystal structures, and the N atom with a bound H atom did not participate in the coordination. In general, this study revealed some interesting findings on the effects of the alkyl-chain structure and the special complexation between pyridylpyrazole ligands and LnIIIions.
Su, Dongping,Liu, Ying,Li, Shimeng,Ding, Songdong,Jin, Yongdong,Wang, Zhipeng,Hu, Xiaoyang,Zhang, Lirong
p. 651 - 658
(2017/02/05)

Mechanistic Studies on Ruthenium(II)-Catalyzed Base-Free Transfer Hydrogenation Triggered by Roll-Over Cyclometalation
The synthesis of 2-substituted pyridine–pyrimidine ligands and their complexation with arene ruthenium(II) chloride moieties is reported. Depending on the electronic and steric influences of the ligand, the catalysts undergo CH activation by roll-over cyclometalation. This process opens up the route to the catalytic transfer hydrogenation of ketones with isopropanol as the hydrogen source under base-free and mild conditions. Barriers related to the roll-over cyclometalation process can be determined experimentally by collision-induced dissociation ESI mass spectrometry. They are supported by DFT calculations and allow the classification of the ligands according to their electronic and steric properties, which is also in accordance with critical bond parameters derived from X-ray structure data. DFT calculations furthermore reveal that the formation of a ruthenium(II) hydrido species is plausible through β-hydride elimination from isopropanol.
Kerner, Christian,Lang, Johannes,Gaffga, Maximilian,Menges, Fabian S.,Sun, Yu,Niedner-Schatteburg, Gereon,Thiel, Werner R.
p. 212 - 224
(2017/03/07)

4-((4-substituted aryl-2-pyrimidinyl) amino) benzoyl hydrazide derivative as well as preparation method and application thereof
The invention provides a 4-((4-substituted aryl-2-pyrimidinyl) amino) benzoyl hydrazide derivative as well as a preparation method and application thereof and relates to a tumor drug. The preparation method comprises the following steps: preparing interme
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Paragraph 0028; 0029

(2017/09/02)

A Rapid and Additive-Free Ruthenium-Catalyzed Reductive Amination of Aromatic Aldehydes
The ruthenium complex [(η6-cymene)Ru(Cl)(dpmpy)]+{dpmpy = 2-[2-(dimethylamino)pyrimidin-4-yl]pyridine} is highly reactive in catalyzing the reductive amination of aromatic aldehydes through in situ generated imines with 2-propanol as the hydrogen source following a transfer-hydrogenation mechanism. This transformation does not require any activating additives and is applicable to a broad variety of aldehydes.
Kerner, Christian,Straub, Sascha-Dominic,Sun,Thiel, Werner R.
p. 3060 - 3064
(2016/07/12)

An optimized approach in the synthesis of imatinib intermediates and analogues
We revisited the classical synthetic procedure for imatinib synthesis providing an improved and optimized approach in the preparation of a series of new imatinib analogues. The proposed methodology effectively overcomes certain problematic steps, saves time and labor, provides a very high yield and purity and has the potential to be used for the synthesis of many analogues. The formation of the desired guanidine salt 4, one of the key steps to the imatinib synthesis, was proceeded almost quantitatively by the reaction of the hydrochloride of the suitable aniline 3 with excess of molten cyanamide, without any solvent. Pure arylamine intermediates 6a-d were obtained quantitatively in a short reaction time after reduction of the nitro group of the intermediate pyrimidines 5a-d with hydrogen over the Adam's catalyst. In addition, the application of this optimized approach can be extended in the synthesis of nilotinib and its analogues intermediates.
Kinigopoulou,Filippidou,Gogou,Giannousi,Fouka,Ntemou,Alivertis,Georgis,Brentas,Polychronidou,Voulgari,Theodorou,Skobridis
p. 61458 - 61467
(2016/07/12)

Metal-Free Route for the Synthesis of 4-Acyl-1,2,3-Triazoles from Readily Available Building Blocks
Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.
Thomas, Joice,Goyvaerts, Vince,Liekens, Sandra,Dehaen, Wim
supporting information
p. 9966 - 9970
(2016/07/19)

Four highly efficient cuprous complexes and their applications in solution-processed organic light-emitting diodes
Four mononuclear cationic Cu(I) complexes featuring functional C-linked pyrazolyl pyridine diimine ligands have been synthesized and characterized. Under UV 365 nm at room temperature, these complexes emit similar orange light in solution and green light
Zhang, Qing,Chen, Xu-Lin,Chen, Jun,Wu, Xiao-Yuan,Yu, Rongmin,Lu, Can-Zhong
p. 34424 - 34431
(2015/04/27)

Selective Extraction of Americium(III) over Europium(III) with the Pyridylpyrazole Based Tetradentate Ligands: Experimental and Theoretical Study
1,3-Bis[3-(2-pyridyl)pyrazol-1-yl]propane (Bippp) and 1,2-bis[3-(2-pyridyl)pyrazyl-1-methyl]benzene (Dbnpp), the pyridylpyrazole based tetradentate ligands, were synthesized and characterized by MS, NMR, and FT-IR. The solvent extraction and complexation
Wang, Jieru,Su, Dongping,Wang, Dongqi,Ding, Songdong,Huang, Chao,Huang, Huang,Hu, Xiaoyang,Wang, Zhipeng,Li, Shimeng
p. 10648 - 10655
(2015/11/27)

OXAZOLIDINONE COMPOUNDS AND THEIR USES IN PREPARATION OF ANTIBIOTICS
The invention belongs to the field of medicaments, and particularly relates to oxazolidinone compounds and their uses in the preparation of antibiotics. A technical problem to be solved by the invention is to provide new oxazolidinone compounds having the structure represented by Formula I. The oxazolidinone compounds of the invention, which are new compounds obtained through numerous screening, have significant antibacterial activity against bacteria such as drug-resistant staphylococcus aureus, fecal coliform bacteria, and streptococcus pneumoniae, while exhibiting low toxicity. The invention provides new options for the development and application of antibiotics.
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Paragraph 0086; 0087; 0088; 0089

(2014/06/24)

A spectroscopic study on the coordination and solution structures of the interaction systems between biperoxidovanadate complexes and the pyrazolylpyridine-like ligands
In order to understand the substitution effects of pyrazolylpyridine (pzpy) on the coordination reaction equilibria, the interactions between a series of pzpy-like ligands and biperoxidovanadate ([OV(O2)2(D 2O)]-/[OV(O2)2(HOD)]-, abbrv. bpV) have been explored using a combination of multinuclear ( 1H, 13C, and 51V) magnetic resonance, heteronuclear single quantum coherence (HSQC), and variable temperature NMR in a 0.15 mol L-1 NaCl D2O solution that mimics the physiological conditions. Both the direct NMR data and the equilibrium constants are reported for the first time. A series of new hepta-coordinated peroxidovanadate species [OV(O2)2L]- (L = pzpy-like chelating ligands) are formed due to several competitive coordination interactions. According to the equilibrium constants for products between bpV and the pzpy-like ligands, the relative affinity of the ligands is found to be pzpy > 2-Ester-pzpy ≈ 2-Me-pzpy ≈ 2-Amide-pzpy > 2-Et-pzpy. In the interaction system between bpV and pzpy, a pair of isomers (Isomers A and B) are observed in aqueous solution, which are attributed to different types of coordination modes between the metal center and the ligands, while the crystal structure of NH4[OV(O2)2(pzpy)]·6H 2O (CCDC 898554) has the same coordination structure as Isomer A (the main product for pzpy). For the N-substituted ligands, however, Isomer A or B type complexes can also be observed in solution but the molar ratios of the isomer are reversed (i.e., Isomer B type is the main product). These results demonstrate that when the N atom in the pyrazole ring has a substitution group, hydrogen bonding (from the H atom in the pyrazole ring), the steric effect (from alkyl) and the solvation effect (from the ester or amide group) can jointly affect the coordination reaction equilibrium. The Royal Society of Chemistry.
Yu, Xian-Yong,Deng, Lin,Zheng, Baishu,Zeng, Bi-Rong,Yi, Pinggui,Xu, Xin
supporting information
p. 1524 - 1533
(2014/01/06)

SUBSTITUTED 3-HETEROARYLOXY-3-(HETERO)ARYL-PROPYLAMINES AS SEROTONIN TRANSPORTER AND SEROTONIN HT2C RECEPTOR MODULATORS
The present invention relates to compounds compound according to Formula (1): and pharmaceutically acceptable salts, hydrates and solvates thereof. These compounds have serotonin (5-HT) transporter inhibitory effects and 5-HT 2C receptor antagonist or inverse agonist effects. The present invention also relates to pharmaceutical compositions comprising these compounds, and methods of using them for application in the prophylaxis or treatment of CNS disorders.
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Page/Page column 12-13; 22

(2014/04/04)

C-H activation at a ruthenium(II) complex - The key step for a base-free catalytic transfer hydrogenation?
Ruthenium(II) complexes [(η6-cymene)RuCl(apypm)]BPh 4 with bidentate 2-amino-4-(2-pyridinyl)pyrimidine (apypm) ligands catalyze the transfer hydrogenation of acetophenone. Their activities are strongly dependent on the substituent pattern of the pyrimidine ring. Complexes bearing a primary amino group in the 2-position of the pyrimidine ring do not perform the catalysis in terms of a "bifunctional mechanism", although they possess protic hydrogen atoms at the amino moiety in close proximity to the metal site. Systems containing tertiary dialkylated amino substituents at the apypm ligand are the first examples of air-stable and phosphane-free transfer-hydrogenation catalysts that show high activities even in the absence of a base. A new mechanism for the catalyst activation in the absence of an external base is proposed on the basis of ESI-MS investigations and ab initio calculations combined with isotope labelling: C-H bond cleavage at the pyrimidine ring is the crucial step for the generation of the catalytically active species. Phosphane-free air-stable ruthenium complexes catalyze the transfer hydrogenation of acetophenone in the absence of a base. Intramolecular C-H bond cleavage gives rise to a new catalyst activation mechanism, which was investigated through isotopic labelling, mass spectrometry and quantum chemical calculations.
Taghizadeh Ghoochany, Leila,Kerner, Christian,Farsadpour, Saeid,Menges, Fabian,Sun, Yu,Niedner-Schatteburg, Gereon,Thiel, Werner R.
p. 4305 - 4317
(2013/09/12)

Synthesis and antibacterial activity of a series of heterocyclic sulfonate ligands and their metal complexes
A series of heterocyclic sulfonate ligands and their barium(II), silver(I), manganese(II), zinc(II) and cobalt(II) coordination compounds have been synthesized. Through antibacterial activities experiments of these complex compounds, metal salts as well as ligands, the rational conclusion is arrived that antibacterial activities of these compounds come from metal ions.
Dong, Hua-Ze,Feng, Xiao-Jun,Dai, Bi-Sheng,Su, Cheng-Bai,Zheng-Zheng,Wang, Lin
p. 2035 - 2037
(2013/05/09)

Structure-reactivity relationships in the hydrogenation of carbon dioxide with ruthenium complexes bearing pyridinylazolato ligands
Pyridinylazolato (N-N') ruthenium(II) complexes of the type [(N-N')RuCl(PMe3)3] have been obtained in high yields by treating the corresponding functionalised azolylpyridines with [RuCl 2(PMe3)4] in the presence of a base. 15N NMR spectroscopy was used to elucidate the electronic influence of the substituents attached to the azolyl ring. The findings are in agreement with slight differences in the bond lengths of the ruthenium complexes. Furthermore, the electronic nature of the azolate moiety modulates the catalytic activity of the ruthenium complexes in the hydrogenation of carbon dioxide under supercritical conditions and in the transfer hydrogenation of acetophenone. DFT calculations were performed to shed light on the mechanism of the hydrogenation of carbon dioxide and to clarify the impact of the electronic nature of the pyridinylazolate ligands. Copyright
Muller, Keven,Sun, Yu,Heimermann, Andreas,Menges, Fabian,Niedner-Schatteburg, Gereon,Van Wuellen, Christoph,Thiel, Werner R.
p. 7825 - 7834
(2013/07/05)

L-proline-catalyzed activation of methyl ketones or active methylene compounds and DMF-DMA for syntheses of (2E)-3-dimethylamino-2- propen-1-ones
A cascade organocatalysis is reported for the nucleophilic and electrophilic dual activation taking place in the reaction of methyl ketones or active methylene compounds with DMF-DMA (N,N-dimethylformamide dimethyl acetal). L-Proline serves as an efficient organocatalyst in the covalent and noncovalent synchronous mode for the ambiphilic activation of various aryl, heteroaryl, and styryl methyl ketones, cyclic ketones, and 1,3-diketones with DMF-DMA to achieve the convenient syntheses of the versatile synthons (2E)-1-aryl/ heteroaryl/styryl-3-(dimethylamino)-2-propen-1-ones, (E)-α- [(dimethylamino)formylidene]cycloalkanones, and (E)-2-(dimethylamino) formylidene-1,3-diketones in high yields under solvent-free conditions.
Kumar, Dinesh,Kommi, Damodara N.,Chopra, Pradeep,Ansari, Md Imam,Chakraborti, Asit K.
p. 6407 - 6413,7
(2020/09/16)

Study of the coordination and solution structures for the interaction systems between diperoxidovanadate complexes and 4-(pyridin-2-yl)pyrimidine-like ligands
To understand the substitution effects of 4-(pyridin-2-yl)pyrimidine (pprd) on the coordination reaction equilibria, the interactions between a series of the pprd-like ligands and [OV(O2)2(H2O)] - or [OV(O2)2(HOD)]- or [OV(O 2)2(D2O)]- (bpV) have been explored by a combination of multinuclear (1H, 13C, and 51V) magnetic resonance, heteronuclear single quantum coherence (HSQC) and variable temperature NMR in a 0.15 mol L-1 NaCl D 2O solution that mimics physiological conditions. The direct NMR data are reported for the first time. Competitive coordination interactions result in a series of new hepta-coordinated peroxidovanadate species [OV(O 2)2LL′]- (LL′ = pprd-like chelating ligands). The equilibrium constants for the products between bpV and the pprd-like ligands show that the relative affinity of the ligands is pprd ≈ 2-NH2-pprd > 2-Me-pprd > 2-Et-pprd > 4-(6-methylpyridin-2- yl)pyrimidine (abbr. 6′-Me-pprd). When the ligand is pprd, a pair of isomers (Isomer A and B) are observed in aqueous solution, which are attributed to the different types of coordination modes between the metal and the ligands, while the crystal structure of NH4[OV(O2) 2(pprd)]·2H2O has the same coordination structure as Isomer A. For substituted pprd ligands, however, only one type of structure (Isomer A or B) is observed in solution. These results demonstrate that, when the aromatic ring has a substitution group, both the steric effect (from the alkyl) and hydrogen bonding (from the amine) can affect the coordination reaction equilibrium to prevent the appearance of either Isomer B in solution for the ligands 2-Me-pprd, 2-NH2-pprd, 2-Et-pprd, or Isomer A in solution for 6′-Me-pprd. The Royal Society of Chemistry 2012.
Yu, Xian-Yong,Yi, Ping-Gui,Ji, Dan-Hong,Zeng, Bi-Rong,Li, Xiao-Fang,Xu, Xin
supporting information; experimental part
p. 3684 - 3694
(2012/05/07)

Synthesis and antimicrobial activity of novel 7-(Heteroaryl)-1,2,4- triazolo[1,5-a]-pyrimidine derivatives
The synthesis, characterization and antimicrobial activity of novel 1,2,4-triazolo[1,5-a]pyrimidines have been reported. The compounds were prepared by acid catalyzed condensation of 3-amino-1,2,4-triazole with 3-(dialkylamino)acryloalkanone.
Rama Rao, R. Janaki,Rao, A.K.S. Bhujanga,Swapna,Rani, B. Baby,Murthy
experimental part
p. 1837 - 1843
(2012/08/07)

Efficient organocatalytic dual activation strategy for preparing the versatile synthons (2 E)-1-(Het)aryl/styryl-3-(dimethylamino)prop-2-en-1-ones and -(E)-[(dimethylamino)methylene]cycloalkanones
A novel organocatalytic dual activation strategy is reported for an efficient synthesis of the versatile synthons (2E)-1-aryl/heteroaryl/styryl-3- (dimethylamino)prop-2-en-1-ones and -(E)-[(dimethylamino)methylene] cycloalkanones. 2-Guanidinoacetic acid (10 mol%) serves as an ambifunctional organocatalyst for the reaction of various aryl/heteroaryl/styryl methyl ketones and cyclic ketones having an -methylene moiety with N,N-dimethylformamide dimethyl acetal at 100 C for 1-3 hours under solvent-free conditions to afford the corresponding (2E)-3-(dimethylamino)prop-2-en-1-ones in 72-95% yields. Georg Thieme Verlag Stuttgart - New York.
Bindal, Sachin,Kumar, Dinesh,Kommi, Damodara N.,Bhatiya, Sonam,Chakraborti, Asit K.
experimental part
p. 1930 - 1935
(2011/07/31)

Synthesis, characterisation and application of iridium(III) photosensitisers for catalytic water reduction
The synthesis of novel, monocationic iridium(III) photosensitisers (Ir-PSs) with the general formula [IrIII(C^N)2(N^N)]+ (C^N: cyclometallating phenylpyridine ligand, N^N: neutral bidentate ligand) is described. The structures obtained were examined by cyclic voltammetry, UV/Vis and photoluminescence spectroscopy and X-ray analysis. All iridium complexes were tested for their ability as photosensitisers to promote homogeneously catalysed hydrogen generation from water. In the presence of [HNEt 3][HFe3(CO)11] as a water-reduction catalyst (WRC) and triethylamine as a sacrificial reductant (SR), seven of the new iridium complexes showed activity. [Ir(6-iPr-bpy)(ppy)2]PF 6 (bpy: 2,2′-bipyridine, ppy: 2-phenylpyridine) turned out to be the most efficient photosensitiser. This complex was also tested in combination with other WRCs based on rhodium, platinum, cobalt and manganese. In all cases, significant hydrogen evolution took place. Maximum turnover numbers of 4550 for this Ir-PS and 2770 for the Fe WRC generated in situ from [HNEt 3][HFe3(CO)11] and tris[3,5- bis(trifluoromethyl)phenyl]phosphine was obtained. These are the highest overall efficiencies for any Ir/Fe water-reduction system reported to date. The incident photon to hydrogen yield reaches 16.4 % with the best system. Copyright
Gaertner, Felix,Cozzula, Daniela,Losse, Sebastian,Boddien, Albert,Anilkumar, Gopinatan,Junge, Henrik,Schulz, Thomas,Marquet, Nicolas,Spannenberg, Anke,Gladiali, Serafino,Beller, Matthias
experimental part
p. 6998 - 7006
(2011/07/29)

Synthesis and antibacterial activity of novel 5-(heteroaryl)isoxazole derivatives
The synthesis, characterization and antibacterial activity of novel isoxazole derivatives were reported. 3-Di (alkylamino)acryloalkanones were prepared and used as synthons to get the target isoxazole derivatives via reaction with hydroxylamine hydrochloride or hydroxylamine-O-sulphonic acid.
RamaRao, R. Janaki,Rao, A.K.S. Bhujanga,Sreenivas,Kumar, B. Suneel,Murthy
experimental part
p. 243 - 250
(2011/06/26)

Novel imatinib derivatives with altered specificity between Bcr-Abl and FMS, KIT, and PDGF receptors
Imatinib is a clinically important ATP analogue inhibitor that targets the tyrosine kinase domain of the intracellular Abl kinase and the PDGF receptor family. Imatinib has revolutionised the treatment of chronic myeloid leukaemia, which is caused by the oncogene Bcr-Abl and certain solid tumours that harbor oncogenic mutations of the PDGF receptor family. As a leading kinase inhibitor, imatinib also provides an excellent model system to investigate how changes in drug design impact biological activity, which is an important consideration for rational drug design. Herein we report a new series of imatinib derivatives that in general have greater activity against the family of PDGF receptors and poorer activity against Abl, as a result of modifications of the phenyl and N-methylpiperazine rings. These new compounds provide a platform for further drug development against the therapeutically important PDGF receptor family and they also provide insight into the engineering of drugs with altered biological activity.
Skobridis, Konstantinos,Kinigopoulou, Maria,Theodorou, Vassiliki,Giannousi, Emilia,Russell, Alison,Chauhan, Rakhee,Sala, Roberta,Brownlow, Nicola,Kiriakidis, Serafim,Domin, Jan,Tzakos, Andreas G.,Dibb, Nick J.
scheme or table
p. 130 - 139
(2010/11/02)

Addressing the poly- to oligo-ketone selectivity in styrene carbonylation catalyzed by palladium/bpy complexes. effect of the 6-alkyl substitution
Two series of organometallic Pd complexes, namely, (i) [Pd(CH 3)(CH3CN)(N-N′)][PF6] and (ii) [Pd(CH3)(N-N′)2][PF6], with a range of 6-alkyl-substituted-2,2′-bipyridine ligands, including the new 6-(1-methoxyethyl)-2,2′-bipyridine, in both racemic and enantiopure form, and 2-(methoxymethyl)-6-(1H-1,2,3-triazol-1-yl)pyridine, have been studied. 6-(1-Methoxyethyl)-2,2′-bipyridine was synthesized both in racemic and in the opposite homochiral enantiomeric forms by two stereocomplementary chemoenzymatic procedures. The characterization of the new complexes, both in solid state and in solution, provides evidence for the formation of a unique isomer featuring the methyl ligand trans to the Pd-N bond of the substituted pyridine ring. For the complex with the bpy ligand having the sec-butyl substituent a cyclometalation reaction with the release of methane occurs, leading the substituted bpy to act as a terdentate N-N′-C ligand. Complexes of series ii feature one chelate N-N′ ligand, while the other one is coordinated to Pd in a monodentate fashion. In solution a fluxional process that makes equivalent the two N-N′ ligands is present, and the static 1H NMR spectra correspond to an averaged structure where palladium is a stereogenic center. All these complexes behave as catalysts for styrene carbonylation, yielding CO/styrene oligoketones, which are optically active when catalysts containing chiral, enantiomerically pure, ligands are applied. For both series of complexes the reactivity with labeled CO has been investigated, leading to the formation of the corresponding Pd-acetyl species, with that for complexes of series ii featuring both N-N′ molecules bonded to the same metal center.
D'Amora, Angela,Fanfoni, Lidia,Cozzula, Daniela,Guidolin, Nicol,Zangrando, Ennio,Felluga, Fulvia,Gladiali, Serafino,Benedetti, Fabio,Milani, Barbara
experimental part
p. 4472 - 4485
(2011/01/06)

Design and synthesis of novel 3,4-disubstituted pyrazoles for nanomedicine applications against malignant gliomas
A series of novel 3,4-disubstituted pyrazoles were synthesized. The cytotoxicity against U87MG glioma cell line have been investigated in vitro and three of these compounds showed promising inhibitory activity on cell growth with an IC50 lower
Comes Franchini, Mauro,Bonini, Bianca Flavia,Camaggi, Carlo Maurizio,Gentili, Denis,Pession, Annalisa,Rani, Monica,Strocchi, Elena
scheme or table
p. 2024 - 2033
(2010/06/20)

6-N-Linked Heterocycle-Substituted 2,3,4,5-Tetrahydro-1H-Benzo[d]Azepines as 5-Ht2c Receptor Agonists
The present invention provides 6-substituted 2,3,4,5-tetrahydro-1H-benzo[d]azepines of Formula I as selective 5-HT2C receptor agonists for the treatment of 5-HT2C associated disorders including obesity, obsessive/compulsive disorder, depression, and anxiety: Formula (I) where: R6 is selected from the group consisting of (a, b, c, d, e) and other substituents are as defined in the specification.
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(2008/12/08)

A facile total synthesis of imatinib base and its analogues
Imatinib and its analogues were successfully synthesized by an improved method in 19.5-46.2% total yield of six main steps. Pyrimidinyl amine was prepared by the reaction of enaminone and guanidine nitrate without the use of a toxic cyanamide. N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl) pyrimidin-2-amine as a key intermediate for the synthesis of imatinib was prepared by coppercatalyzed iV-arylation of heteroarylamme in 82% yield. The copper salts were used instead of the expensive palladium compounds in this C-N bond-forming reaction. The intermediate nitro compound was reduced by a N2H 4.H2O/FeCl3/C system using water as a solvent in good yield.
Liu, Yi-Feng,Wang, Cui-Ling,Bai, Ya-Jun,Han, Ning,Jiao, Jun-Ping,Qi, Xiao-Li
p. 490 - 495
(2013/01/03)

Microwave assisted condensation reactions of 2-aryl hydrazonopropanals with nucleophilic reagents and dimethyl acetylenedicarboxylate
The reaction of methyl ketones 1a-g with dimethylformamide dimethylacetal (DMFDMA) afforded the enaminones 2a-g, which were coupled with diazotized aromatic amines 3a,b to give the corresponding aryl hydrazones 6a-h. Condensation of compounds 6a-h with so
Al-Zaydi, Khadijah M.,Borik, Rita M.
p. 2061 - 2079
(2008/02/08)

Synthesis of a new series of pyrazolo[1,5-a]pyrimidines structurally related to zaleplon
(Chemical Equation Presented) The reaction between 3-(dimethylamino)/3,3- bis(methylthio)-1-(substituted)prop-2-en-1-ones and 4-substituted-5-amino-1H- pyrazoles afforded new pyrazole[1,5-a]pyrimidines structurally related to Zaleplon. The chemical modifications introduced at the 3-, 5-, and 7-positions of the bicyclic structure revealed new promising candidates for the treatment of sleep disorders.
Baraldi, Pier Giovanni,Fruttarolo, Francesca,Tabrizi, Mojgan Aghazadeh,Romagnoli, Romeo,Preti, Delia,Ongini, Ennio,El-Kashef, Hussein,Carrion, Maria Dora,Borea, Pier Andrea
p. 355 - 361
(2008/04/12)

Pyrazolo[1,5-a]pyrimidin-7-yl phenyl amides as novel antiproliferative agents: Exploration of core and headpiece structure-activity relationships
A novel series of antiproliferative agents containing pyrazolo[1,5-a]pyrimidin-7-yl phenyl amides, selective for p21-deficient cells, were identified by high-throughput screening. Exploration of the SAR relationships in the headpiece, core, and tailpiece
Powell, Dennis,Gopalsamy, Ariamala,Wang, Yanong D.,Zhang, Nan,Miranda, Miriam,McGinnis, John P.,Rabindran, Sridhar K.
p. 1641 - 1645
(2007/10/03)

INHIBITORS OF HISTONE DEACETYLASE
The invention relates to a series of compounds useful for inhibiting histone deacetylase (HDAC) enzymatic activity. The invention also provides a method for inhibiting histone descetylase in a cell using said compounds as well as a method for treating cell proliferative diseases and conditions using said HDAC inhibitors. Further, the invention provides pharmaceutical compositions comprising the HDAC inhibiting compounds and a pharmaceutically acceptable carrier.
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(2010/02/14)