- Redox deracemization of phosphonate-substituted dihydropyrimidines
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An efficient redox deracemization of the phosphonic ester substituted 3,4-dihydropyrimidin-2-one (DHPM) derivatives is described. The one-pot deracemization strategy consisted of the oxidization to destroy the stereocenter center and the following asymmetric transfer hydrogenation to regenerate the chiral carbon center with the vicinal phosphonic ester group, providing a series of optically active phosphonate substituted DHPMs with up to 96% ee.
- Feng, Guang-Shou,Guo, Xuan,Meng, Fan-Jie,Shao, Bing-Ru,Shi, Lei,Velopolcek, Maria K.
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supporting information
p. 10570 - 10574
(2021/12/27)
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- Continuous synthesis method of 2-chloropyrimidine-4-formic acid compound
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The invention provides a continuous synthesis method of a 2-chloropyrimidine-4-formic acid compound. The 2-chloropyrimidine-4-formic acid compound has a structure represented by a formula I, wherein in the formula I, R1 and R2 are respectively and independently selected from hydrogen, alkoxy, aryl, benzyl or fluorine. The synthesis method comprises the following steps: S1, under the action of a non-noble metal catalyst, carrying out continuous methylation reaction on a compound A and a methyl Grignard reagent B to obtain a compound C, wherein the compound A is a compound shown in the specification, the compound C is a compound shown in the specification, R1 and R2 are respectively and independently selected from hydrogen, alkoxy, aryl, benzyl or fluorine, and the non-noble metal catalyst is one or more of ferric salt, cobalt salt and nickel salt; and S2, carrying out continuous oxidation reaction on the compound C under the action of oxygen, an oxidation catalyst and an additive, and thus obtaining the 2-chloropyrimidine-4-formic acid compound. By adopting the process provided by the invention to synthesize the 2-chloropyrimidine-4-formic acid compound, the aspects of cost, yield,environmental friendliness and the like can be considered.
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Paragraph 0045; 0047-0055
(2020/01/25)
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- ANDROGEN RECEPTOR MODULATORS AND METHODS FOR USE AS PROTEOLYSIS TARGETING CHIMERA LIGANDS
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The present invention relates to bifunctional Proteolysis Targeting Chimeric ligands (Protac compounds) comprising a ligase modulator/binder and a molecule that binds to a protein target of interest, and methods of treating various diseases and conditions with the Protac compounds, including diseases associated with androgen receptors.
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Paragraph 788-789
(2020/10/20)
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- Synthesis and biological activity of novel dimethylpyrazole and piperazine-containing (bis)1,2,4-triazole derivatives
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A series of novel dimethylpyrazole and piperazine-containing (bis)1,2,4-triazole derivatives have been conveniently synthesized via Mannich reaction in good yields. Their structures were identified by IR,1H NMR,13C NMR, and elemental analysis. The preliminary bioassays showed that among 14 new compounds, the trifluoromethyl-containing compounds exhibited superior activity than the methyl-containing ones; some of the compounds displayed significant in vitro and in vivo fungicidal activity against several plant fungi and were comparable with the control Triadimefon; several compounds exhibited certain herbicidal activity against Brassica campestris; several compounds possessed favorable KARI inhibitory activity, especially 8D could be a promising KARI inhibitor for further study. The research results will provide useful information for the design and discovery of new agrochemicals with novel heterocyclic Mannich base structures containing piperazine moiety.
- Wang, Bao-Lei,Zhang, Yan,Liu, Xing-Hai,Zhang, Li-Yuan,Zhan, Yi-Zhou,Zhang, Xiao,Wang, Li-Zhong,Li, Yong-Hong,Li, Zheng-Ming
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- 6-substituted pyrimidyl quinazolinone compound and application thereof
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The invention discloses a 6-substituted pyrimidyl quinazolinone compound having a novel structure represented as the general formula (I) and a salt thereof, wherein the substituent groups in the formula are defined as the specification. The compound has excellent insecticidal activity and can be used for preventing and treating insect pests in agriculture, forestry or non-treatment target, especially, the application for preventing and treating aphids.
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Paragraph 0117; 0118; 0119
(2016/10/09)
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- Method for preparing 2-chloropyrimidine-4 formic acid
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The invention relates to a method for preparing 2-chloropyrimidine-4 formic acid. The method comprises the following steps: performing debydrochlorination reaction on 2-chlorine-4-methyl pyridine hydrochloride and phosphorus oxychloride and separating, thereby acquiring 2-chlorine-4-methyl pyridine; and performing methyl oxidizing reaction on 2-chlorine-4-methyl pyridine and methyl oxidant and separating, thereby acquiring 2-chloropyrimidine-4 formic acid. According to the process route provided by the invention, the yield of the target product is high, the process route can be amplified, the raw materials can be easily acquired and have low cost, and industrial production can be carried out.
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Paragraph 0016; 0017; 0018
(2017/01/02)
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- Synthesis and Fungicidal Activities of Novel 1,2,4-Triazole Thione Derivatives Containing 1,2,3-Triazole and Substituted Piperazine Moieties
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A series of novel 1,2,4-triazole thione derivatives containing 1,2,3-triazole and substituted piperazine moieties were synthesized via the Mannich reaction of 1,2,3-triazole-containing 1,2,4-triazole thiol intermediates with various substituted piperazines and formaldehyde in high yields. The structures of 14 title compounds were confirmed by melting points, IR, 1H NMR, 13C NMR, and elemental analysis. The bioassay results showed that some of the title compounds exhibit significant fungicidal activities against several plant fungi at 50 μg/mL, especially trifluoromethyl-containing triazole thione derivative 9g showed broad activities and could be made further structural optimization for novel fungicides innovation research.
- Wang, Bao-Lei,Zhan, Yi-Zhou,Zhang, Li-Yuan,Zhang, Yan,Zhang, Xiao,Li, Zheng-Ming
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-
- Synthesis and biological activity of novel N-glucosides containing substituted piperazine moiety
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A series of novel acetylated piperazine-containing N-glucosides and bis(N-glucoside) 8a-i were synthesized by the nucleophilic addition of acetylated glucopyranosyl isothiocyanate with various substituted piperazines in THF with high yields. Their novel deacetylated products 9a-i were also synthesized after Me-ONa/MeOH treatment. The preliminary bioassays for 18 novel title compounds showed that several compounds have significant fungicidal activity against Fusarium omysporum, Cercospora arachidicola and Phytophthora capsici at 50 μg/mL.
- Zhang, Li-Yuan,Wang, Bao-Lei,Zhan, Yi-Zhou,Hua, Xue-Wen,Liu, Ming,Zhang, Xiao,Song, Hai-Bin,Li, Zheng-Ming
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p. 343 - 351
(2016/04/04)
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- Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties
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A series of novel carboxamide compounds 19a-19j, 20a-20j and 22a-22d containing piperazine and arylsulfonyl moieties have been synthesized. The bioassay results showed that some compounds exhibited favorable herbicidal activities against dicotyledonous plants and many of them possessed excellent antifungal activities. Among 24 novel compounds, some showed superiority over the commercial fungicides Chlorothalonil, Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin at 500 mg/L concentration. Some compounds also exhibited high KARI inhibitory activity at 100 γ1/4g/mL concentration and could be used as new KARI lead inhibitors for further studies. Moreover, SAR of these new compounds were comprehensively investigated using different computational methods in which 3D-QSAR model obtained provided useful information for further structural optimization for the discovery of new fungicides. The results of this research will contribute to explore comprehensive biological activities of piperazine-containing compounds in different areas of chemistry.
- Wang, Bao-Lei,Shi, Yan-Xia,Zhang, Shu-Jun,Ma, Yi,Wang, Hong-Xue,Zhang, Li-Yuan,Wei, Wei,Liu, Xing-Hai,Li, Yong-Hong,Li, Zheng-Ming,Li, Bao-Ju
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p. 167 - 178
(2016/04/26)
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- Synthesis and biological activities of novel 1,2,4-triazole thiones and bis(1,2,4-triazole thiones) containing phenylpyrazole and piperazine moieties
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A series of novel 1,2,4-triazole thione and bis(1,2,4-triazole thione) derivatives containing phenylpyrazole and substituted piperazine moieties have been conveniently synthesized via Mannich reaction using various 1,2,4-triazole thiols, substituted piperazines, and formaldehyde at room temperature in short time. Their structures were confirmed by IR, 1H NMR, 13C NMR and elemental analysis. The preliminary bioassays for 27 new title compounds have shown that some of them possess certain herbicidal activities against Echinochloa crusgalli at 100 μg/mL concentration. Some of the compounds exhibited significant in vitro fungicidal activities, especially against Cercospora arachidicola and Rhizoctonia cerealis at the concentration of 50 μg/mL, and were comparable with that of control Triadimefon. Meanwhile, IXp held the control efficacy of 60% against Puccinia sorghi Schw. at 200 μg/mL concentration in the in vivo test. The SAR analysis has indicated that compounds with two CF3 groups both on triazole and pyrazole rings are more effective than compounds with one CF3 group or two CH3 groups according to their fungicidal activity data. On the whole, compounds VIIIg, IXi, IXo and IXp could be used as novel lead structures for the design and discovery of new fungicides.
- Wang, Bao-Lei,Zhang, Li-Yuan,Zhan, Yi-Zhou,Zhang, Yan,Zhang, Xiao,Wang, Li-Zhong,Li, Zheng-Ming
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-
- Synthesis and Biological Activity of Novel Furan/Thiophene and Piperazine-Containing (Bis)1,2,4-triazole Mannich Bases
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Series of novel furan/thiophene and piperazine-containing 1,2,4-triazole Mannich bases and bis(1,2,4-triazole) Mannich bases have been conveniently synthesized via Mannich reaction with triazole Schiff bases, various piperazine derivatives, and formaldehyde as intermediates in good yields. Their structures were characterized by melting points, 1H NMR, 13C NMR, IR and elemental analysis. The preliminary bioassay showed that most compounds exhibited significant in vitro and in vivo fungicidal activity against several test plant fungi. Among 32 new compounds, the trifluoromethyl-containing compounds showed superior activity than the methyl-containing ones. Several compounds, such as F8, F9, F10, G5, H7, H8, I3 and I4, were comparable with some commercial fungicides against different fungi during the present study and could be further structurally optimized. Meanwhile, several compounds showed good herbicidal activity against Brassica campestris at 100 μg/mL and KARI inhibitory activity at 200 μg/mL. However, compounds exhibited poor insecticidal activity against oriental armyworm at 200 μg/mL in the preliminary studies. The research results will provide useful information for the design and discovery of new agrochemicals with novel heterocyclic structures.
- Wang, Baolei,Shi, Yanxia,Zhan, Yizhou,Zhang, Liyuan,Zhang, Yan,Wang, Lizhong,Zhang, Xiao,Li, Yonghong,Li, Zhengming,Li, Baoju
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p. 1124 - 1134
(2015/11/02)
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- Synthesis, crystal structure and DFT studies of N-[4-(Heptyloxy)phenyl]-4-methylpyrimidin-2-amine
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The compound N-[4-(heptyloxy)phenyl]-4-methylpyrimidin-2-amine with the molecular formula C18H25N3O was synthesized and recrystallized from CH3OH. The compound was characterized by 1H NMR, MS, HRMS and X-ray diffraction. The compound crystallized in the monoclinic space group P2(1)/c with a = 9.426 (2), b = 14.434 (3), c = 12.884 (3) ?, α = 90, β = 93.779 (3), γ = 90°, V = 1749.2 (6) ?3, Z = 4 and R = 0.0402 for 1798 observed reflections with I > 2σ(I). Theoretical calculation of the title compound was carried out with B3LYP/6-31G (d, p). The full geometry optimization was carried out using 6-31G (d, p) basis set and the frontier orbital energy. The optimized geometric bond lengths and bond angles obtained by using DFT(B3LYP) show the best agreement with the experimental data.
- Wu, Lei-Ting,Sun, Na-Bo,He, Fang-Yue
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p. 7397 - 7400
(2015/04/22)
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- Synthesis and biological activity of some novel trifluoromethyl-substituted 1,2,4-triazole and bis(1,2,4-Triazole) mannich bases containing piperazine rings
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A series of trifluoromethyl-substituted 1,2,4-triazole Mannich base 6 and bis(1,2,4-triazole) Mannich base 7 containing pyrimidinylpiperazine rings via the Mannich reaction were synthesized and characterized by infrared (IR), 1H nuclear magnetic resonance (NMR), and elemental analysis. The fungicidal tests indicated that most of compounds 6 and 7 possessed excellent fungicidal activity. Among 19 novel compounds, some showed superiority over commercial fungicides Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin. Some compounds also exhibited favorable herbicidal activity in the preliminary studies. On the basis of the comparative molecular field analysis (CoMFA), five novel compounds were subsequently synthesized, their activities were estimated fairly accurately, and compounds 6-A1 and 7-A2 displayed good fungicidal activity against Pseudoperonospora cubensis (96.9 and 84.9%) as 6h and 7c, respectively.
- Wang, Bao-Lei,Shi, Yan-Xia,Ma, Yi,Liu, Xing-Hai,Li, Yong-Hong,Song, Hai-Bin,Li, Bao-Ju,Li, Zheng-Ming
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scheme or table
p. 5515 - 5522
(2011/08/03)
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- THIAZOLE AND OXAZOLE KINASE INHIBITORS
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The present invention provides thiazole and oxazole compounds, compositions containing the same, as well as processes for the preparation and methods for their use as pharmaceutical agents.
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Page/Page column 110
(2009/07/17)
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- (3-HYDROXY-4-AMINO-BUTAN-2-YL) -3- (2-THIAZOL-2-YL-PYRROLIDINE-1-CARBONYL) BENZAMIDE DERIVATIVES AND RELATED COMPOUNDS AS BETA-SECRETASE INHIBITORS FOR TREATING
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The present invention provides novel beta-secretase inhibitors and methods for their use, including methods of treating of Alzheimer's disease. (Formula)
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Page/Page column 83
(2009/05/29)
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- Novel HIV reverse transcriptase inhibitors
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The invention is related to compounds of Formula (I), (II), or (III): or a pharmaceutically acceptable salt, solvate, ester, and/or phosphonate thereof, compositions containing such compounds, and therapeutic methods that include the administration of such compounds.
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Page/Page column 41-42
(2008/06/13)
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- PHENYL-[4-(3-PHENYL-1H-PYRAZOL-4-YL)-PYRIMIDIN-2-YL]-AMINE DERIVATIVES AS IGF-IR INHIBITORS
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The present invention relates to a compound of formula (I) and derivatives thereof. Furthermore, the invention relates to the use of such compounds as medicaments. In addition, the invention relates to the use of such compounds for manufacturing a medicament useful for treating proliferative diseases.
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Page/Page column 37-38
(2008/06/13)
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- PHENYL-[4-(3-PHENYL-1H-PYRAZOL-4-YL)-PYRIMIDIN-2-Yl)-AMINE DERIVATIVES
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The invention relates to phenyl-[4-(3-phenyl-1H-pyrazol-4-yl)-pyrimidin-2-yl)-amine derivatives and to processes for the preparation thereof, to pharmaceutical compositions comprising such derivatives and to the use of such derivatives - alone or in combination with one or more other pharmaceutically active compounds - for the preparation of pharmaceutical compositions for the treatment especially of a proliferative disease, such as a tumour.
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-
- Selective iron-catalyzed cross-coupling reactions of Grignard reagents with enol triflates, acid chlorides, and dichloroarenes
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Cheap, readily available, air stable, nontoxic, and environmentally benign iron salts such as Fe(acac)3 are excellent precatalysts for the cross-coupling of Grignard reagents with alkenyl triflates and acid chlorides. Moreover, it is shown that dichloroarene and -heteroarene derivatives as the substrates can be selectively monoalkylated by this method. All cross-coupling reactions proceed very rapidly under notably mild conditions and turned out to be compatible with a variety of functional groups in both reaction partners. A detailed analysis of the preparative results suggests that iron-catalyzed C-C bond formations can occur via different pathways. Thus, it is likely that reactions of methylmagnesium halides involve iron-ate complexes as the active components, whereas reactions of Grignard reagents with two or more carbon atoms are effected by highly reduced iron-clusters of the formal composition [Fe(MgX)2]n generated in situ. Control experiments using the ate-complex [Me4Fe]Li2 corroborate this interpretation.
- Scheiper, Bodo,Bonnekessel, Melanie,Krause, Helga,Fuerstner, Alois
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p. 3943 - 3949
(2007/10/03)
-
- PEPTIDE DEFORMYLASE INHIBITORS
-
Novel PDF inhibitors and novel methods for their use are provided.
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- 1-(Aromatic- or heteroaromatic-substituted)-3-(heteroaromatic substituted)-1,3-propanediones and uses thereof
-
Certain 1-(aromatic- or heteroaromatic-substituted-3-(heteroaromatic substituted)-1,3-propanediones are described as inhibitors of HIV integrase and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.
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- 1N-ALKYL-N-ARYLPYRIMIDINAMINES AND DERIVATIVES THEREOF
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The present invention provides novel compounds, compounds and pharmaceutical compositions thereof, and methods of using same in the treatment of affective disorders, anxiety, depression, post-traumatic stress disorders, eating disorders, supranuclear palsy, irritable bowel syndrome, immune suppression, Alzheimer'disease, gastrointestinal diseases, anorexia nervosa, drug and alcohol withdrawal symptoms, drug addiction, inflammatory disorders, or fertility problems. The novel compounds provided by this invention are those of formula: wherein R 1, R 3, R 4, R 5, Z, Y, V, X, X', J, K, L, and M are as defined herein.
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- 1N-alkyl-N-arylpyrimidinamines and derivatives thereof
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The present invention provides novel compounds, compounds and pharmaceutical compositions thereof, and methods of using same in the treatment of affective disorders, anxiety, depression, post-traumatic stress disorders, eating disorders, supranuclear palsy, irritable bowel syndrome, immune suppression, Alzheimer's disease, gastrointestinal diseases, anorexia nervosa, drug and alcohol withdrawal symptoms, drug addiction, inflammatory disorders, or fertility problems. The novel compounds provided by this invention are those of formula: wherein R1, R3, R4, R5, Z, Y, V, X, X', J, K, L, and M are as defined herein.
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- The synthesis of substituted pyridylpyrimidine fungicides using palladium-catalysed cross-coupling reactions
-
Various substituted phenyl, pyridyl and benzyl zinc chlorides have been generated from the corresponding lithium or magnesium organometallic reagents. These have been cross-coupled with 2-(6-bromo-2- pyridyl)pyrimidines in the presence of tetrakis(triphenylphosphine)palladium(0) to produce a series of substituted pyridylpyrimidine fungicides in 32-99% yields. (C) 2000 Elsevier Science Ltd.
- Hargreaves, Stephanie L.,Pilkington, Brian L.,Russell, Sally E.,Worthington, Paul A.
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p. 1653 - 1656
(2007/10/03)
-
- Pyrolysis of 1-substituted pyrazoles and chloroform at 550°C: Formation of α-carboline from 1-benzylpyrazoles
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Pyrolysis of 13CH3 labelled 1-methylpyrazole 8 with chloroform at 550°C in a continuous flow reactor yields unlabelled 2-chloropyrimidine 9 and 2-cyanopyrrole 10 labelled at the cyano group. However, pyrolysis of 1-benzylpyrazole 14 with chloroform under similar conditions gives 9,2-phenylpyrimidine 13 and, as the major product, α-carboline 15. Pyrolysis of several substituted 1-(arylmethyl)pyrazoles and the use of 13C and 15N labelled compounds provides direct evidence by which the positions of 7 atoms of 1-benzylpyrazole can be located in the α-carboline. These data support the mechanisms suggested for the formation of 9, 10, and 15.
- Bhatti, Inayat A.,Busby, Reginald E.,Bin Mohamed, Murtedza,Parrick, John,Shaw, C. J. Granville
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p. 3581 - 3585
(2007/10/03)
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- Trialkylalanes in palladium-catalyzed C-alkylations of azines
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Carbo-substitution with alkyl groups in halogenoazines is readily effected under the influence of Pd-catalysis with alanes as the donor of the alkyl group. Acta Chemica Scandinavica 1997.
- Lu, Qingbo,Mangalagiu, Lonel,Benneche, Tore,Undheim, Kjell
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p. 302 - 306
(2007/10/03)
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- Pyri(mi)dyl-oxy-and -thio-benzoic acid derivatives useful as herbicides and plant growth regulants
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New pyri(mi)dyl-oxy- or -thio-benzoic acid derivatives of the formula STR1 are taught which have herbicidal and plant growth regulating activity. In the formula Z can be Ch or N, X is oxygen or sulphur, A is oxygen, sulphur, a radical R5 --N=or a radical R6 O--N=and B is oxygen, sulphur, a radical STR2 with the proviso that at least one of the radicals R1, R2 or R3 represents alkyl or a part of a 3- to 6-membered fused carbocyclic ring.
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