cas 7504-94-1, 2(1H)-Pyrimidinone, hydrazone (9CI)

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Synthesis, crystal structures, and magnetic properties of methoxido-bridged dinuclear MnIII complexes derived from tri-dentate chelating ligands
Two new doubly methoxido-bridged MnIII dinuclear complexes, [MnIII(mphp)(μ-OCH3)(CH3OH)]2·2CH3OH (1) and ([MnIII(ahbz)(μ-OCH3)(CH3OH)]2·2CH3
Yuan, Juan,Chu, Yi-Xin,Kou, Hui-Zhong
p. 1218 - 1225
(2016)
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Synthesis and antiviral activity of nonannulated tetrazolylpyrimidines
[Figure not available: see fulltext.] Nonannulated tetrazolylpyrimidines in the structure of which the heterocyclic fragments are separated by hydrazinocarbonylmethyl, methylpyrazolyl groups or a sulfur atom were synthesized. Some of these compounds showed moderate in vitro activity against H1N1 subtype of influenza A virus. The selectivity index of the anti-influenza action of {5-[(4,6-dimethylpyrimidin-2-yl)sulfanyl]-1H-tetrazol-1-yl}acetic acid, which has very low cytotoxicity, was twice as high as the selectivity index of the reference drug rimantadine.
Ostrovskii, Vladimir А.,Danagulyan, Gevorg G.,Nesterova, Olga M.,Pavlyukova, Yulia N.,Tolstyakov, Vladimir V.,Zarubina, Olga S.,Slepukhin, Pavel А.,Esaulkova, Yana L.,Muryleva, Anna А.,Zarubaev, Vladimir V.,Trifonov, Rostislav E.
p. 448 - 454
(2021/05/21)

Tetrahydroindazole inhibitors of CDK2/cyclin complexes
Over 50 tetrahydroindazoles were synthesized after 7-bromo-3,6,6-trimethyl-1-(pyridin-2-yl)-5,6,7,7a-tetrahydro-1H-indazol-4(3aH)-one (3) was identified as a hit compound in a high throughput screen for inhibition of CDK2 in complex with cyclin A. The activity of the most promising analogues was evaluated by inhibition of CDK2 enzyme complexes with various cyclins. Analogues 53 and 59 showed 3-fold better binding affinity for CDK2 and 2- to 10-fold improved inhibitory activity against CDK2/cyclin A1, E, and O compared to screening hit 3. The data from the enzyme and binding assays indicate that the binding of the analogues to a CDK2/cyclin complex is favored over binding to free CDK2. Computational analysis was used to predict a potential binding site at the CDK2/cyclin E1 interface.
Lee, Jae Chul,Hong, Kwon Ho,Becker, Andreas,Tash, Joseph S.,Sch?nbrunn, Ernst,Georg, Gunda I.
(2021/02/09)

Metal free [4+1] and [5+1] annulation reactions to prepare heterocycles using DMF and its derivatives as one-carbon source
1,2,4-Triazolo[3,4-a]pyridines and related heterocycles and substituted triazines were commonly discovered scaffolds in a variety of pharmaceutical and agrochemical agents. Herein, we report a highly efficient and practical method using DMF and its derivative for the [4+1] and [5+1] annulation reactions to prepare these heterocycles. This metal free reaction takes advantages of shelf stable DMF as solvent and carbon donor, imidazole chloride as a catalyst, the mild reaction condition tolerates a broad substrate range and substitutes. The prepared 3-unsubstituted 1,2,4-triazolo[3,4-a]pyridine and derivatives allow further introduction of a variety of functional group1 at 3-position.
Liu, Lingfeng,Qiao, Chunhua,Shen, Bei,Xu, Yiwen
supporting information

(2020/04/01)

NNO type quinoline Fe (II) complex containing multiple coordination sites as well as preparation method and application of NNO type quinoline Fe (II) complex
The invention discloses an NNO type quinoline Fe (II) complex containing multiple coordination sites as well as a preparation method and application of the NNO type quinoline Fe (II) complex. The complex is a quinoline-2-formaldehyde-benzoyl hydrazone Fe
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Paragraph 0060-0061

(2020/10/20)

Azacyclopyrimidine hydrazone Zn (II) complex containing multiple coordination sites as well as preparation method and application thereof
The invention discloses an azacyclo pyrimidine hydrazone Zn (II) complex containing multiple coordination sites as well as a preparation method and application of the azacyclo pyrimidine hydrazone Zn(II) complex. The complex is a 5-chloropyridine-2-formaldehyde 2-pyrimidine hydrazone Zn (II) complex, and the molecular formula of the complex is [Zn (C10H8N5Cl) 2]. 2ClO4. 2CH3OH. Experimental results show that the pyrimidine hydrazone Zn (II) complex prepared by the preparation method disclosed by the invention has a remarkable inhibition effect on various tumor cell strains such as human breast cancer cells MCF-7, human gastric cancer cells BGC-823, lung cancer cells A549 and liver cancer cells BEL-7402; the inhibitory activity is obviously better than that of a positive control drug 5-FU,the inhibitory effect on gastric cancer cells BGC-823 and liver cancer cells BEL-7402 is particularly remarkable, and IC50 values are only 3.22 [mu] M and 3.91 [mu] M respectively. Meanwhile, it is found that the inhibition effect of the pyrimidine hydrazone Zn (II) complex on tumor cells is obviously higher than that of a ligand 5-chloropyridine-2-formaldehyde 2-pyrimidine hydrazone used alone.Therefore, the pyrimidine hydrazone Zn (II) complex disclosed by the invention has good in-vitro anti-tumor activity and is expected to be developed into an anti-tumor drug.
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Paragraph 0039-0044

(2020/10/14)

Hydrazone bond-containing pyrimidine hydrazine derivative transition metal cobalt (II) complex as well as preparation method and application thereof
The invention discloses a hydrazone bond-containing pyrimidine hydrazine derivative transition metal cobalt (II) complex as well as a preparation method and application thereof, wherein the complex isa 6-bromopyridine-2-formaldehyde pyrimidine-2-hydrazone cobalt (II) complex, and the molecular formula of the complex is [Co2(C10H8N5Br)4].4ClO4.H2O. Experimental results show that the hydrazone bond-containing pyrimidine hydrazine derivative transition metal cobalt (II) complex prepared by the preparation method disclosed by the invention has an obvious inhibition effect on two tumor cells of human gastric cancer cells BGC-823 and lung cancer cells A549 and has the inhibition activity better than that of 6-bromopyridine-2-formaldehyde pyrimidine-2-hydrazone derivatives and a broad-spectrum anti-tumor drug 5-fluorouracil which are independently used, but basically has no inhibition effect on two tumor cells of human breast cancer cells MCF-7 and liver cancer cells BEL-7402. Therefore, thehydrazone bond-containing pyrimidine hydrazine derivative transition metal cobalt (II) complex has cell selectivity in antitumor activity, can be effectively used for preparing antitumor drug lead compounds, and is an innovation in antitumor drugs.
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Paragraph 0036-0041; 0063-0064

(2020/11/02)

NNN type pyrimidine hydrazone cobalt (II) complex containing quinoline structure as well as preparation method and application thereof
The invention discloses an NNN type pyrimidine hydrazone cobalt (II) complex containing a quinoline structure as well as a preparation method and application thereof. The NNN type pyrimidine hydrazonecobalt (II) complex is a cobalt (II) complex based on a quinoline-2-formaldehyde 2-pyrimidine hydrazone ligand, and the molecular formula of the NNN type pyrimidine hydrazone cobalt (II) complex is [Co (C14H11N5) 2]. 2ClO4. H2O. According to the invention, the antioxidant activity of the complex is researched by adopting a DPPH method; results show that the complex has a strong scavenging effecton DPPH free radicals and is far higher than vitamin E with the same concentration, the antioxidant activity is remarkably enhanced along with increase of the concentration, and when the concentrationis 1 mg/mL, the scavenging rate of the compound on the DPPH free radicals reaches up to 77.77%. Therefore, the NNN-type pyrimidine hydrazone cobalt (II) complex containing the quinoline structure hasa good in-vitro antioxidant effect, can be effectively used for preparing anti-aging drugs, and is an innovation of anti-aging drugs.
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Paragraph 0038; 0041-0043

(2020/10/14)

Activating Pyrimidines by Pre-distortion for the General Synthesis of 7-Aza-indazoles from 2-Hydrazonylpyrimidines via Intramolecular Diels-Alder Reactions
Pyrimidines are almost unreactive partners in Diels-Alder cycloadditions with alkenes and alkynes, and only reactions under drastic conditions have previously been reported. We describe how 2-hydrazonylpyrimidines, easily obtained in two steps from commercially available 2-halopyrimidines, can be exceptionally activated by trifluoroacetylation. This allows a Diels-Alder cycloaddition under very mild reaction conditions, leading to a large diversity of aza-indazoles, a ubiquitous scaffold in medicinal chemistry. This reaction is general and scalable and has an excellent functional group tolerance. A straightforward synthesis of a key intermediate of Bayer's Vericiguat illustrates the potential of this cycloaddition strategy. Quantum mechanical calculations show how the simple N-trifluoroacetylation of 2-hydrazonylpyrimidines distorts the substrate into a transition-state-like geometry that readily undergoes the intramolecular Diels-Alder cycloaddition.
Le Fouler, Vincent,Chen, Yu,Gandon, Vincent,Bizet, Vincent,Salomé, Christophe,Fessard, Thomas,Liu, Fang,Houk,Blanchard, Nicolas
supporting information
p. 15901 - 15909
(2019/10/22)

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF
Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.
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Paragraph 1484

(2018/04/17)

Structure-based discovery and synthesis of potential transketolase inhibitors
Transketolase (TKL) plays a key role in plant photosynthesis and has been predicted to be a potent herbicide target. Homology modeling and molecular dynamics simulation were used to construct a target protein model. A target-based virtual screening was developed to discover novel potential transketolase inhibitors. Based on the receptor transketolase 1 and a target-based virtual screening combined with structural similarity, six new compounds were selected from the ZINC database. Among the structural leads, a new compound ZINC12007063 was identified as a novel inhibitor of weeds. Two novel series of carboxylic amide derivatives were synthesized, and their structures were rationally identified by NMR and HRMS. Biological evaluation of the herbicidal and antifungal activities indicated that the compounds 4u and 8h were the most potent herbicidal agents, and they also showed potent fungicidal activity with a relatively broad-spectrum. ZINC12007063 was identified as a lead compound of potential transketolase inhibitors, 4u and 8h which has the herbicidal and antifungal activities were synthesized based on ZINC12007063. This study lays a foundation for the discovery of new pesticides.
Huo, Jingqian,Zhao, Bin,Zhang, Zhe,Xing, Jihong,Zhang, Jinlin,Dong, Jingao,Fan, Zhijin
(2018/09/11)

Discovery of KDM5A inhibitors: Homology modeling, virtual screening and structure-activity relationship analysis
Herein we report the discovery of a series of new KDM5A inhibitors. A three-dimensional (3D) structure model of KDM5A jumonji domain was firstly established based on homology modeling. Molecular docking-based virtual screening was then performed against c
Wu, Xiaoai,Fang, Zhen,Yang, Bo,Zhong, Lei,Yang, Qiuyuan,Zhang, Chunhui,Huang, Shenzhen,Xiang, Rong,Suzuki, Takayoshi,Li, Lin-Li,Yang, Sheng-Yong
supporting information
p. 2284 - 2288
(2016/04/20)

Proton transfer reactions of N-aryl triazolium salts: Unusual ortho-substituent effects
Previous studies of the C(3)-hydrogen/deuterium exchange reactions of the triazolium ion conjugate acids of triazolyl N-heterocyclic carbenes revealed a change of mechanism under acidic conditions with N1-protonation to a dicationic salt. Interestingly, the data suggested an increase in pKaN1 in the presence of a N-pentafluorophenyl substituent relative to other N-aryl substituents with hydrogens or methyl substituents rather than fluorines at the ortho-positions. To probe the presence of an apparent donor effect of a N-pentafluorophenyl substituent, which differs from the more common electron withdrawing effect of this group, we have studied the analogous deuterium exchange reactions of four triazolium salts with heteroatoms or heteroatom substituents in the 2-position and/or 6-position of the N-aryl ring. These include triazolium salts with N-2,4,6-tribromophenyl 11, N-2,6-dichlorophenyl 12, N-2-pyridyl 13 and N-2-pyrimidinyl 14 substituents. The log kex - pD profiles for 11, 12 and 14 were found to show similar trends at lower pDs as for the previously studied N-pentafluorophenyl triazolium salt, hence supporting the presence an apparent donor effect on pKaN1. Surprisingly, the log kex - pD profile for N-pyridyl salt 13 uniquely showed acid catalysis at lower pDs. We propose herein that this data is best explained by invoking an intramolecular general base role for the N-(2-pyridyl) substituent in conjunction with N1-protonation on the triazolium ring. Finally, the second order rate constants for deuteroxide ion catalysed C(3)-H/D exchange (kDO, M-1 s-1), which could be obtained from data at pDs 1.5, were used to provide estimates of C(3)-carbon acid pKaC3 values for the four triazolium salts 11-14.
Tucker, David E.,Quinn, Peter,Massey, Richard S.,Collett, Christopher J.,Jasiewicz, David J.,Bramley, Christopher R.,Smith, Andrew D.,O'Donoghue, AnnMarie C.
supporting information
p. 108 - 115
(2015/03/04)

Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs
A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5- methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects.
Nakao, Syuhei,Mabuchi, Miyuki,Shimizu, Tadashi,Itoh, Yoshihiro,Takeuchi, Yuko,Ueda, Masahiro,Mizuno, Hiroaki,Shigi, Naoko,Ohshio, Ikumi,Jinguji, Kentaro,Ueda, Yuko,Yamamoto, Masatatsu,Furukawa, Tatsuhiko,Aoki, Shunji,Tsujikawa, Kazutake,Tanaka, Akito
supporting information
p. 1071 - 1074
(2014/03/21)

Synthesis and in vitro activity of novel 1,2,4-triazolo[4,3-a]pyrimidine oxazolidinone antibacterial agents
The synthesis and antibacterial activity of 3-(4-([1,2,4]triazolo[4,3-a] pyrimidin-3-yl)phenyl)oxazolidin-2-ones is reported. Thiocarbonyl derivatives were found to be potent inhibitors of Gram-positive pathogens and compound 4l was two to fourfold more p
Khera, Manoj K.,Cliffe, Ian A.,Mathur, Tarun,Prakash, Om
scheme or table
p. 2887 - 2889
(2011/06/24)

Synthesis and in vitro activity of novel 1,2,4-triazolo[4,3-a]pyrimidine oxazolidinone antibacterial agents. Part II
The synthesis and antibacterial activity of 1,2,4-triazolo[4,3-a]pyrimidine oxazolidinones is reported. Compound 3e with a 2,4-disubstituted thiophene ring was found to be a potent inhibitor of Gram-positive pathogens and was 4-16-fold more potent than Linezolid.
Khera, Manoj Kumar,Cliffe, Ian A.,Prakash, Om
scheme or table
p. 5266 - 5269
(2011/10/02)

AZO PIGMENT, PIGMENT DISPERSION CONTAINING THE AZO PIGMENT, AND COLORING COMPOSITION
Provided is an azo pigment having excellent coloring characteristics such as high tinctorial strength and hue and having excellent durability such as high resistance to light and ozone, a pigment dispersion containing the azo pigment, and a coloring composition. An azo pigment represented by the following general formula (1), a tautomer of the azo pigment, and a salt or a hydrate thereof: (In the general formula (1), G0 and G1 each independently represents a non-metal atomic group which can form a 5- or 6-membered heterocyclic ring wherein each heterocyclic ring may be unsubstituted or may have a substituent; each heterocyclic ring may be a monocyclic ring or a condensed ring; X represents a hetero atom; n represents an integer of 1 to 4; when n = 2, the compound of formula (1) represents a dimer formed via A or a heterocyclic group represented by G0 or G1;. when n = 3, the compound of formula (1) represents a trimer formed via A and/or a heterocyclic group represented by G0 or C1; when n = 4, the compound of formula (1) represents a tetramer formed via A and/or a heterocyclic group represented by G0 or G1; A represents any one selected from the group of the specific substituents.)
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Page/Page column 164

(2011/01/11)

2-[4-(PYRAZOL-4-YLALKYL)PIPERAZIN-1-YL]-3-PHENYL PYRAZINES AND PYRIDINES AND 3-[4-(PYRAZOL-4-YLALKYL)PIPERAZIN-1-YL]-2-PHENYL PYRIDINES AS 5-HT7 RECEPTOR ANTAGONISTS
The present invention provides selective 5-HT7 receptor antagonist compounds of Formula I and their use in the treatment of migraine, persistent pain, and anxiety: where A and B are each independently C(H)= or N=, provided that at least one of A and B is -N=, n is 1-3, m is 0-3, and R14 are as defined herein.
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Page/Page column 58

(2009/01/20)

PYRAZOLE AND PYRROLE COMPOUNDS USEFUL IN TREATING IRON DISORDERS
This invention is directed to pyrazole and pyrrole compounds, for example, compounds of formula (I): wherein R1, R2, R3 and R4 are as defined herein, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of iron disorders. This invention is also directed to pharmaceutical compositions comprising the compounds and methods of using the compounds to treat iron disorders.
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Page/Page column 65

(2008/12/04)

PYRAZOLE DERIVATIVES
A compound represented by formula (I): (wherein Ar1 represents a phenyl group which may have 1 to 3 substituents, or a non-substituted 5- or 6-membered aromatic heterocyclic group; Ar2 represents (i) a non-substituted phenyl group, (ii) a phenyl group which has been substituted by a lower alkyl group having 1 to 3 groups or atoms selected from among a carbamoyl group, an amino group, a hydroxyl group, a lower alkoxy group, and a halogen atom, or (iii) a 5- or 6-membered nitrogen-containing aromatic heterocyclic group which has been substituted by 1 to 3 groups or atoms selected from among a lower alkyl group, a lower alkynyl group, a lower alkanoyl group, a carbamoyl group, a cyano group, an amino group, a hydroxyl group, a lower alkoxy group, and a halogen atom; and X represents a group represented by formula (II): (wherein the ring structure represents a 4- to 7-membered heterocyclic group which may have, in addition to the nitrogen atom shown in formula (II), one heteroatom selected from among nitrogen, oxygen, and sulfur, and which may be substituted by 1 to 4 groups or atoms selected from among a lower alkyl group, a carbamoyl group, an amino group, a hydroxyl group, a lower alkoxy group, an oxo group, a lower alkanoyl group, a lower alkylsulfonyl group, and a halogen atom)), a salt thereof, a solvate of the compound or the salt, and a drug.
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Page/Page column 22-23

(2010/11/26)

AMIDOPYRAZOLE DERIVATIVE
A platelet coagulation inhibitor which inhibits neither COX-1 nor COX-2 is provided. The inhibitor is a compound represented by general formula (I): wherein Ar1 and Ar2 independently represent a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents, or a phenyl group optionally substituted with 1 to 3 substituents; R1 represents a lower acyl group, carboxyl group, a lower alkoxycarbonyl group, a lower alkoxy group, a lower alkyl group optionally substituted with 1 or 2 substituents, a carbamoyl group optionally substituted with 1 or 2 substituents, an oxamoyl group optionally substituted with 1 or 2 substituents, an amino group optionally substituted with 1 or 2 substituents, a 4- to 7-membered alicyclic heterocyclic group optionally substituted with 1 or 2 substituents, a phenyl group optionally substituted with 1 to 3 substituents, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents; and R2 represents hydrogen atom, a halogeno group, or the like.
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Page/Page column 47-48

(2010/11/23)

Condensed pyrazole derivatives, process for producing the same and use thereof
Novel pharmaceutical compositions for inhibiting Th2-selective immune response and pharmaceutical compositions for inhibiting cyclooxygenase comprising condensed pyrazole derivatives represented by the general formula (I): or salts thereof.
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(2008/06/13)

Synthesis and mechanism of action of novel pyrimidinyl pyrazole derivatives possessing antiproliferative activity
Pyrimidinyl pyrazole derivatives 1-4, prepared as a new scaffold of an anti-tumor agent, showed antiproliferative activity against human lung cancer cell lines and inhibited tubulin polymerization. Furthermore, it was found that compound 2 bound at the colchicine site on tubulin, but the tubulin binding pattern was different from that of colchicine. Here, we describe the synthesis of the derivatives and the differences of the action mechanism on tubulin polymerization inhibition between compound 2 and colchicine.
Ohki, Hitoshi,Hirotani, Kenji,Naito, Hiroyuki,Ohsuki, Satoru,Minami, Megumi,Ejima, Akio,Koiso, Yukiko,Hashimoto, Yuichi
p. 3191 - 3193
(2007/10/03)

Toward enediyne mimics: Methanolysis of azoesters and a bisazoester
Enediyne anticancer antibiotics have attracted tremendous interest in the past decade. The inherent difficulty in synthesizing these structurally complex natural products with the strained enediyne moiety has motivated a search for simpler molecules that mimic enediyne chemistry. The ultimate objective is to identify molecules that produce 1,4-benzenoid diradicals, which are known to induce DNA cleavage in the natural products. Toward this goal, several aromatic azoesters have been synthesized, and EPR reveals the presence of radical intermediates in their methanolysis. A 1,4-bisazoester has also been synthesized, and its methanolysis products have been studied by reversed-phase HPLC. The formation of 1,2-dicyanobenzene from the 1,4- bisazoester is consistent with the existence of a 1,4-diradical intermediate.
Srinivasan, Veeraraghavan,Jebaratnam, David J.,Budil, David E.
p. 5644 - 5649
(2007/10/03)

PYRAZOLINE COMPOUNDS AND USE AS PLANT DISEASE CONTROL AGENT
A pyrazoline compound represented by the formula (I): wherein R1represents a phenyl group which may be substituted, R2represents a hydrocarbon group which may be substituted, R3represents an alkyl group or the like, R4and R5, which may be the same or different, represent a hydrogen atom or the like, A and B, which may be the same or different, represents a group CH or the like, is used as an effective ingredient of plant disease controlling agent.
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(2008/06/13)

Amino-substituted pyrimidines, derivatives and methods of use therefor
The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation end products of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.
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(2008/06/13)