cas 18740-38-0, 2,4-Dihydroxythieno[2,3-d]pyrimidine

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Ionic liquid promoted synthesis of heterocycle-fused pyrimidine-2,4(1H,3H)-diones utilising CO2
An efficient ionic liquid system was developed for the preparation of various heterocycle-fused pyrimidine-2, 4(1H,3H)-diones in moderate to excellent yields (52–95%). It was found that [HDBN+][TFE?], a simple and easily prepared ionic liquid, could act as both the solvent and reaction promoter, and that the reactions could be efficiently carried out at atmospheric pressures of CO2.
Li, Chun,Lu, Xunhua,Yang, Yuanyong,Yang, Shenggang,Zhang, Lin
p. 2463 - 2466
(2018)
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Design, synthesis, and biological evaluation of novel thienopyrimidine derivatives as PI3Kα inhibitors
Three series of novel thienopyrimidine derivatives 9a-l, 15a-l, and 18a-h were designed and synthesized, and their IC50 values against four cancer cell lines HepG-2, A549, PC-3, and MCF-7 were evaluated. Most compounds show moderate cytotoxicity against the tested cancer cell lines. The most promising compound 9a showed moderate activity with IC50 values of 12.32 ± 0.96, 11.30 ± 1.19, 14.69 ± 1.32, and 9.80 ± 0.93 μM, respectively. The inhibitory activities of compounds 9a and 15a against PI3Kα and mTOR kinase were further evaluated. Compound 9a exhibited PI3Kα kinase inhibitory activity with IC50 of 9.47 ± 0.63 μM. In addition, docking studies of compounds 9a and 15a were also investigated.
Yu, Lide,Wang, Qinqin,Wang, Caolin,Zhang, Binliang,Yang, Zunhua,Fang, Yuanying,Zhu, Wufu,Zheng, Pengwu
(2019/10/02)

Preparation method of heterocyclicpyrimidinedione compound
The invention discloses a preparation method of a heterocyclicpyrimidinedione compound and relates to the technology of medicinal chemistry. The preparation method comprises the following steps: 1) mixing an o-amino formonitrile heterocyclic compound and a catalyst to form a mixture, wherein the catalyst is [HDBN][TFE]; 2) in a CO2 environment, heating the mixture and reacting; 3) when the temperature is reduced to room temperature, adjusting the pH value to neutrality, and extracting, separating and collecting the an organic phase; drying, filtering and then vaporizing; performing column chromatography separation to obtain the heterocyclicpyrimidinedione compound. The preparation method disclosed by the invention has the advantages of low cost, environmental friendliness, simple preparation process and wide application range of substrate.
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Paragraph 0051; 0052; 0053

(2018/03/26)

Design, Synthesis, and SAR Studies of Heteroarylpyrimidines and Heteroaryltriazines as CB2R Ligands
Herein we describe the design and synthesis of a new series of heteroarylpyrimidine/heteroaryltriazine derivatives on the basis of quinazoline-2,4(1H,3H)-diones as CB2R-selective ligands using a bioisosterism strategy. An acetamide group was explored to displace the enamine linker of the lead compound for the purpose of stereoisomerism elimination and hydrophilicity increase. As a result, some of the synthesized compounds showed high bioactivity and selectivity for CB2R in calcium mobilization assays, and four displayed CB2R agonist activity, with EC50 values below 30 nm. The compound exhibiting the highest agonist activity toward CB2R (EC50=7.53±3.15 nm) had a selectivity over CB1R of more than 1328-fold. Moreover, structure–activity relationship (SAR) studies indicated that the substituents on the nucleus play key roles in the functionality of a ligand, with one such example demonstrating CB2R antagonist activity. Additionally, molecular docking simulations were conducted with the aim of better understanding of these new derivatives in relation to the structural requirements for agonists/antagonists binding to CB2R.
Qian, Hai-Yan,Wang, Zhi-Long,Chen, Li-Li,Pan, You-Lu,Xie, Xiao-Yu,Xie, Xin,Chen, Jian-Zhong
supporting information
p. 2455 - 2463
(2018/11/23)

Heterocyclic-pyrimindine or pyrazine compound containing biarylamide structure and application thereof
The invention discloses a heterocyclic-pyrimindine or pyrazine compound containing a biarylamide structure. The heterocyclic-pyrimindine or pyrazine compound is as shown in a general formula I or II, wherein the general formula I and the general formula II are shown in the description. The heterocyclic-pyrimindine or pyrazine compound containing the biarylamide structure, and pharmaceutically acceptable salts, hydrates or solvates thereof are used as active components, and are mixed with a pharmaceutically acceptable carrier or excipient to prepare a composition; and the composition is prepared into clinically acceptable preparations. The compound provided by the invention can be used for treating and/or preventing proliferative diseases, and treating and/or preventing prostate cancer, lung cancer and cervical cancer.
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Paragraph 0088; 0089; 0090

(2017/07/22)

The structure containing [...] of thienopyrimidines preparation and application
The invention discloses a thienopyrimidine compound containing a chromone hydrazone structure, a geometrical isomer of the compound, pharmaceutically acceptable salts, hydrates, solvates or prodrugs of the compound, as well as application of the compound to preparation of medicines for treating and/or preventing hyperplastic diseases, application of the compound to preparation of medicines for treating and/or preventing cancers and application of the compound to preparation of medicines for treating and/or preventing lung cancers, liver cancers, gastric cancers, colon cancers and breast cancers.
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Paragraph 0148; 0149; 0150

(2016/11/21)

Heteroarylpyrimindinedione derivative and use thereof
The invention provides a heteroarylpyrimindinedione derivative and use thereof. The heteroarylpyrimindinedione derivative comprises a compound with a structure shown as general formula I, and a pharmaceutically acceptable salt or hydrate thereof. The derivative is obtained by chemical synthesis, and pharmacological experiments prove that the active ligand with cannabinoid type II receptor CB2 can be used for preparation of drugs for prevention and mitigation of CB2 receptor-mediated diseases, and the drug is cannabinoid CB2 receptor agonist's agonist, partial agonist, inverse agonist or antagonist. And the general structural formula I is shown as the specification.
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Paragraph 0225; 0226; 0227

(2017/04/03)

Design, synthesis and docking studies of novel thienopyrimidine derivatives bearing chromone moiety as mTOR/PI3Kα inhibitors
Two series of thienopyrimidine derivatives (10a-k, 16a-j) bearing chromone moiety were designed and synthesized. All the compounds were evaluated for inhibitory activity against mTOR kinase at a concentration of 10uM. Four selected compounds were further evaluated for the IC50 values against mTOR kinase, PI3Kα kinase and two cancer cell lines. Some of the target compounds exhibited moderate to excellent mTOR/PI3Kα kinase inhibitory activity and cytotoxicity. The most promising compound 16i showed good inhibitory activity against mTOR/PI3Kα kinase and good antitumor potency for H460 and PC-3 cell lines with IC50 values of 0.16 ± 0.03 μM, 2.35 ± 0.19 μM, 1.20 ± 0.23 μM and 0.85 ± 0.04 μM, which were 8.6, >5, 7.9 and 19.1 times more active than compound I (1.37 ± 0.07 μM, >10 μM, 9.52 ± 0.29 μM, 16.27 ± 0.54 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that the chromone moiety is necessary for the potent antitumor activity and cytotoxicity of these compounds. Substitution of the chromone moiety at the 6-position has a significant impact to the inhibitory activity, in particular a carboxylic acid group, produced the best potency.
Zhu, Wufu,Chen, Chen,Sun, Chengyu,Xu, Shan,Wu, Chunjiang,Lei, Fei,Xia, Hui,Tu, Qidong,Zheng, Pengwu
p. 64 - 73
(2015/02/19)

Identification of 2,4-diamino-6,7-dimethoxyquinoline derivatives as G9a inhibitors
G9a is a histone lysine methyltransferase (HKMT) involved in epigenetic regulation via the installation of histone methylation marks. 6,7-Dimethoxyquinazoline analogues, such as BIX-01294, are established as potent, substrate competitive inhibitors of G9a. With an objective to identify novel chemotypes for substrate competitive inhibitors of G9a, we have designed and synthesised a range of heterocyclic scaffolds, and investigated their ability to inhibit G9a. These studies have led to improved understanding of the key pharmacophoric features of BIX-01294 and the identification of a new core quinoline inhibitory scaffold, which retains excellent potency and high selectivity. Molecular docking was carried out to explain the observed in vitro data. This journal is
Srimongkolpithak, Nitipol,Sundriyal, Sandeep,Li, Fengling,Vedadi, Masoud,Fuchter, Matthew J.
p. 1821 - 1828
(2015/01/08)

Rational design of phosphoinositide 3-kinase inhibitors that exhibit selectivity over the phosphoinositide 3-kinase isoform
Of the four class I phosphoinositide 3-kinase (PI3K) isoforms, PI3K has justly received the most attention for its potential in cancer therapy. Herein we report our successful approaches to achieve PI3K vs PI3K selectivity for two chemical series. In the thienopyrimidine series of inhibitors, we propose that select ligands achieve selectivity derived from a hydrogen bonding interaction with Arg770 of PI3K that is not attained with the corresponding Lys777 of PI3K. In the benzoxepin series of inhibitors, the selectivity observed can be rationalized by the difference in electrostatic potential between the two isoforms in a given region rather than any specific interaction.
Heffron, Timothy P.,Wei, Binqing,Olivero, Alan,Staben, Steven T.,Tsui, Vickie,Do, Steven,Dotson, Jennafer,Folkes, Adrian J.,Goldsmith, Paul,Goldsmith, Richard,Gunzner, Janet,Lesnick, John,Lewis, Cristina,Mathieu, Simon,Nonomiya, Jim,Shuttleworth, Stephen,Sutherlin, Daniel P.,Wan, Nan Chi,Wang, Shumei,Wiesmann, Christian,Zhu, Bing-Yan
experimental part
p. 7815 - 7833
(2012/01/05)

Selective kainate receptor (GluK1) ligands structurally based upon 1H-cyclopentapyrimidin-2,4(1 H,3 H)-dione: Synthesis, molecular modeling, and pharmacological and biostructural characterization
The physiological function of kainate receptors (GluK1-GluK5) in the central nervous system is not fully understood yet. With the aim of developing potent and selective GluK1 ligands, we have synthesized a series of new thiophene-based GluK1 agonists (6a-c) and antagonists (7a-d). Pharmacological evaluation revealed that they are selective for the GluK1 subunit, with 7b being the most subtype-selective ligand reported to date (GluK1 vs GluK3). The antagonist 7a was cocrystallized with the GluK1 ligand binding domain, and an X-ray crystallographic analysis revealed the largest flexibility in GluK1 ligand binding domain opening upon binding of a ligand seen to date. The results provide new insights into the molecular mechanism of GluK1 receptor ligand binding and pave the way to the development of new tool compounds for studying kainate receptor function.
Venskutonytè, Raminta,Butini, Stefania,Sanna Coccone, Salvatore,Gemma, Sandra,Brindisi, Margherita,Kumar, Vinod,Guarino, Egeria,Maramai, Samuele,Valenti, Salvatore,Amir, Ahmad,Valadés, Elena Antón,Frydenvang, Karla,Kastrup, Jette S.,Novellino, Ettore,Campiani, Giuseppe,Pickering, Darryl S.
experimental part
p. 4793 - 4805
(2011/10/01)

The highly potent and selective dipeptidyl peptidase IV inhibitors bearing a thienopyrimidine scaffold effectively treat type 2 diabetes
New dipeptidyl peptidase IV inhibitors were designed based on Alogliptin using a scaffold-hopping strategy. All of the compounds constructed on a thienopyrimidine scaffold demonstrated good inhibition and selectivity for DPP-IV. Compound 10d exhibited subnanomolar (IC50 = 0.33 nM) DPP-IV inhibitory activity, good in vivo efficacy and an acceptable pharmacokinetic profile. A pharmacokinetic-driven optimization of 10d may lead to a new class of clinical candidate DPP-IV inhibitors.
Deng, Jifeng,Peng, Li,Zhang, Guicheng,Lan, Xiaobing,Li, Chufang,Chen, Fuxin,Zhou, Yayao,Lin, Zuoxian,Chen, Ling,Dai, Renke,Xu, Hongjiang,Yang, Ling,Zhang, Xiquan,Hu, Wenhui
experimental part
p. 71 - 76
(2011/02/25)

A convenient synthesis of new 3,7-diphenylthieno[3,2-e]bis[1,2,4] triazolo[4,3-a:4',3'-c]pyrimidine derivatives by oxidative cyclization Using alumina-supported calcium hypochlorite
New 3,7-diphenylthieno[3,2-e]bis[1,2,4]triazolo[4,3-a:4',3'-c]pyrimidine derivatives were easily synthesized at room temperature in good yield by the oxidative cyclization of thienopyrimidinyl hydrazones with alumina-supported calcium hypochlorite (Ca(OCl
Son, Hoon Young,Song, Yang-Heon
scheme or table
p. 2242 - 2246
(2010/11/05)

THIENOPYRIMIDIENE DERIVATIVES AS PI3K INHIBITORS
Thienopyrimidines of formula (I) wherein W and R1 to R4 are as defined in the claims, and the pharmaceutically acceptable salts thereof are inhibitors of PI3K and are selective for the p110δ isoform, which is a class Ia PI3 kinase, over both other class Ia and class Ib kinases. The compounds may be used to treat diseases and disorders arising from abnormal cell growth, function or behaviour associated with PI3 kinase such as cancer, immune disorders, cardiovascular disease, viral infection, inflammation, metabolism/endocrine function disorders and neurological disorders.
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Page/Page column 81

(2009/05/28)

COMPOUNDS ACTIVE ON GLUTAMATERGIC RECEPTORS
The present invention relates to a compound of Formula (I) process for its preparation and uses thereof.
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Page/Page column 13

(2008/06/13)

PHOSPHOINOSITIDE 3-KINASE INHIBITOR COMPOUNDS AND METHODS OF USE
Compounds of Formulas Ia-d where X is S or O, mor is a morpholine group, and R3 is a monocyclic heteroaryl group, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for modulating the activity of lipid kinases including PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formula Ia-d for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed. Formula (Ic) and (Id).
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Page/Page column 169

(2008/12/06)

4-CYANOPHENYLAMINO-SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS HIV INHIBITORS
This application concerns certain 4-cyanophenylamino-substituted bicyclic heterocycles of formula (I) where the dashed line represents a double bond that may be located either between A and C(V) or between C(V) and D, where A is S or C(Z); D is S or C(W); provided that one and only one of A and D is S; where T is NH, O, or S; and where other substituents are defined herein. These compounds are non-nucleoside reverse transcriptase inhibitors and have potential as anti-HIV treatment.
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Page/Page column 44

(2008/12/05)

THIENO [2,3-D] PYRIMIDINE COMPOUNDS AS INHIBITORS OF ADP-MEDIATED PLATELETS AGGREGATION
Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I): wherein A1, A2, A3, A4, A5, A6, A7, A8, X4, X6, R2, R4, R5, and R6 are as defined in the detailed description of the invention. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.
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Page/Page column 92

(2008/06/13)

PYRAZOLE DERIVATIVES AS INHIBITORS OF RECEPTOR TYROSYNE KINASES
Compounds of formula (I): and their use in the inhibition of Trk activity are described.
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Page/Page column 108

(2008/06/13)

Process for controlling eradicating or preventing infestations of animals by Ixodid ticks
A process for the prevention of infestation by Ixodid ticks, or for the control or eradication of infestations of Ixodid ticks, which process comprises applying to the media to be protected or to the infested media an effective amount of a composition com
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(2008/06/13)

Thienopyrimidines
Thienopyrimidines of the formula: STR1 wherein R1 is straight or branched chain alkyl containing from 3 to 11 carbon atoms and optionally substituted with cyano or methoxy, cycloalkyl, benzyl optionally substituted on the α carbon atom with a l
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(2008/06/13)