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7-Benzyloxy-4-chloro-6-methoxyquinazoline is a chemical compound belonging to the quinazoline class of organic compounds. It is a derivative of quinazoline, a bicyclic heterocyclic compound with a benzene ring fused to a pyrimidine ring. 7-Benzyloxy-4-chloro-6-methoxyquinazoline features a chloro group at the 4th position, a methoxy group at the 6th position of the quinazoline ring, and a benzyloxy group attached to the 7th position. Its unique chemical structure and properties make it a valuable tool for researchers and scientists in various fields, particularly in the pharmaceutical industry for the development of new drugs and molecular probes for biological studies.

162364-72-9

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162364-72-9 Usage

Uses

Used in Pharmaceutical Industry:
7-Benzyloxy-4-chloro-6-methoxyquinazoline is used as a chemical compound for the development of new drugs and molecular probes for biological studies. Its specific chemical structure and properties make it a valuable tool for researchers and scientists in the field of pharmaceuticals.
Used in Drug Development:
7-Benzyloxy-4-chloro-6-methoxyquinazoline is used as a potential candidate in drug development due to its unique chemical structure and properties. It can be utilized in the design and synthesis of new drugs targeting various diseases and conditions.
Used in Molecular Probes for Biological Studies:
7-Benzyloxy-4-chloro-6-methoxyquinazoline is used as a molecular probe in biological studies to investigate the interactions between biological molecules and drug candidates. Its specific chemical structure allows for targeted studies and the development of novel therapeutic approaches.

Check Digit Verification of cas no

The CAS Registry Mumber 162364-72-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,2,3,6 and 4 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 162364-72:
(8*1)+(7*6)+(6*2)+(5*3)+(4*6)+(3*4)+(2*7)+(1*2)=129
129 % 10 = 9
So 162364-72-9 is a valid CAS Registry Number.
InChI:InChI=1/C16H13ClN2O2/c1-20-14-7-12-13(18-10-19-16(12)17)8-15(14)21-9-11-5-3-2-4-6-11/h2-8,10H,9H2,1H3

162364-72-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-chloro-6-methoxy-7-phenylmethoxyquinazoline

1.2 Other means of identification

Product number -
Other names 4-Chloro-6-methoxy-7-benzyloxyquinazoline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:162364-72-9 SDS

162364-72-9Relevant articles and documents

Discovery of quinazoline derivatives as a novel class of potent and in vivo efficacious LSD1 inhibitors by drug repurposing

Li, Zhonghua,Li, Zhongrui,Ma, Jinlian,Miao, Jinxin,Qin, Tingting,Yang, Nian,Zhang, Xinhui,Zhang, Zhenqiang,Zhao, Taoqian,Zhao, Xuan

, (2021/08/19)

Histone lysine-specific demethylase 1 (LSD1) is an important epigenetic modulator, and is implicated in malignant transformation and tumor pathogenesis in different ways. Therefore, the inhibition of LSD1 provides an attractive therapeutic target for cancer therapy. Based on drug repurposing strategy, we screened our in-house chemical library toward LSD1, and found that the EGFR inhibitor erlotinib, an FDA-approved drug for lung cancer, possessed low potency against LSD1 (IC50 = 35.80 μM). Herein, we report our further medicinal chemistry effort to obtain a highly water-soluble erlotinib analog 5k (>100 mg/mL) with significantly enhanced inhibitory activity against LSD1 (IC50 = 0.69 μM) as well as higher specificity. In MGC-803 cells, 5k suppressed the demethylation of LSD1, indicating its cellular activity against the enzyme. In addition, 5k had a remarkable capacity to inhibit colony formation, suppress migration and induce apoptosis of MGC803 cells. Furthermore, in MGC-803 xenograft mouse model, 5k treatment resulted in significant reduction in tumor size by 81.6% and 96.1% at dosages of 40 and 80 mg/kg/d, respectively. Our findings indicate that erlotinib-based analogs provide a novel structural set of LSD1 inhibitors with potential for further investigation, and may serve as novel candidates for the treatment of LSD1-overexpressing cancers.

Heterocyclic compound, preparation method and application thereof

-

, (2020/07/02)

The invention relates to a heterocyclic compound in the technical field of medicines. The compound is represented by a structural general formula I or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, X, Y, Z, Cy1, Cy2, m, n and t have the meanings given in the specification; in addition, the invention also discloses an application of the compound and the pharmaceuticallyacceptable salt thereof in preparation of drugs for treating diseases caused by abnormal high expression of tyrosine kinase, especially application in preparation of drugs for treating and preventingcancers.

Structure–activity relationship study of novel quinazoline-based 1,6-naphthyridinones as MET inhibitors with potent antitumor efficacy

Zhuo, Lin-Sheng,Wu, Feng-Xu,Wang, Ming-Shu,Xu, Hong-Chuang,Yang, Fan-Peng,Tian, Yan-Guang,Zhao, Xing-E.,Ming, Zhi-Hui,Zhu, Xiao-Lei,Hao, Ge-Fei,Huang, Wei

, (2020/09/09)

As a privileged scaffold, the quinazoline ring is widely used in the development of EGFR inhibitors, while few quinazoline-based MET inhibitors are reported. In our ongoing efforts to develop new MET-targeted anticancer drug candidates, a series of quinaz

Design, synthesis and biological evaluation of novel 4-anilinoquinazoline derivatives as hypoxia-selective EGFR and VEGFR-2 dual inhibitors

Wei, Huiqiang,Duan, Yuqing,Gou, Wenfeng,Cui, Jie,Ning, Hongxin,Li, Deguan,Qin, Yong,Liu, Qiang,Li, Yiliang

, (2019/08/07)

Tyrosine kinase inhibitors (TKIs) have achieved substantial clinical effects for cancer treatment while causing a number of adverse effects. Since hypoxia is an intrinsic difference between solid tumor and healthy tissues, one strategy to overcome the adverse effects of TKIs is to enhance the specificity of anti-tumor activity by selectively targeting hypoxic region of tumors. Herein, we designed and synthesized a series of novel 4-anilinoquinazoline derivatives by introducing 3-nitro-1,2,4-triazole group to the side chain of vandetanib with modification of aniline moiety. Lead compounds, 10a and 10g, exhibited potent inhibitory activity against EGFR and VEGFR-2 kinase. Moreover, these two compounds were shown to enhance anti-proliferative activities on A549 and H446 cells under hypoxic conditions compared to vandetanib and dramatically down-regulate VEGF gene expression. In vivo studies confirmed that 10a and 10g not only inhibited tumor growth in A549 xenografts of BALB/c-nu mice but also significantly reduce toxicity associated with weight loss compared to vandetanib. These results suggest that EGFR/VEGFR-2 dual inhibitors, 10a and 10g, emerged as potential hypoxia-selective anti-tumor drugs with less toxicity for inhibiting in vitro and in vivo models of non-small cell lung cancer cells.

Design and discovery of 4-anilinoquinazoline-urea derivatives as dual TK inhibitors of EGFR and VEGFR-2

Zhang, Hai-Qi,Gong, Fei-Hu,Ye, Ji-Qing,Zhang, Chi,Yue, Xiao-Hong,Li, Chuan-Gui,Xu, Yun-Gen,Sun, Li-Ping

, p. 245 - 254 (2016/10/03)

EGFR and VEGFR-2 are involved in pathological disorders and the progression of different kinds of tumors, the combined blockade of EGFR and VEGFR signaling pathways appears to be an attractive approach to cancer therapy. In this work, a series of 4-anilinoquinazoline derivatives containing substituted diaryl urea or glycine methyl ester moiety were designed and identified as EGFR and VEGFR-2 dual inhibitors. Compounds 19i, 19j and 19l exhibited the most potent inhibitory activities against EGFR (IC50?=?1?nM, 78?nM and 51?nM, respectively) and VEGFR-2 (IC50?=?79?nM, 14?nM and 14?nM, respectively), they showed good antiproliferative activities as well. Molecular docking established the interaction of 19i with the DFG-out conformation of VEGFR-2, suggesting that they might be type II kinase inhibitors.

Epidermal growth factor receptor tyrosine kinase inhibitors MPGF and MPGH with anti-tumor activity and preparation method and application thereof

-

Paragraph 0044; 0049, (2016/10/27)

The invention discloses epidermal growth factor receptor tyrosine kinase inhibitors (EGFR TKI) MPGF and MPGH with the anti-tumor activity and a preparation method and application thereof. By optimizing and improving the chemical structure of PD153035, brand-new EGFR TKIs are obtained and named as MPGF (shown in the formula I) and MPGH (shown in the formula II). Research shows that the synthesized EGFR TKI-MPGF and EGFR TKI-MPGH can effectively inhibit tumor cell proliferation and has a stronger proliferation inhibition effect on mutational EGFR lung cancer cell line PC-9 compared with the PD153035, and therefore the EGFR TKI-MPGF and the EGFR TKI-MPGH can serve as anti-tumor agents to be applied in clinic. In addition, the invention discloses the method for preparing the epidermal growth factor receptor tyrosine kinase inhibitors (EGFR TKI) MPGF and MPGH with the anti-tumor activity. By means of the epidermal growth factor receptor tyrosine kinase inhibitors (EGFR TKI) MPGF and MPGH with the anti-tumor activity and the preparation method and application thereof, an effective technological means is provided for tumor treatment, especially for treatment of the non-small cell lung cancer.

4-substituted anilinoquinazoline derivatives, and preparation method and application thereof

-

Paragraph 0062; 0063, (2017/01/31)

The invention discloses novel 4-substituted anilinoquinazoline derivatives or pharmaceutically acceptable salts thereof, or polymorphic substances, solvates or stereomers of the 4-substituted anilinoquinazoline derivatives, and a preparation method and application thereof. The 4-substituted anilinoquinazoline compounds have favorable inhibition activities for EGFR and VEGFR-2 in a biological test and have obvious effects in an in-vitro anti-human tumor cell proliferation activity test.

QUINAZOLINE COMPOUNDS

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Paragraph 00264; 00265; 00266; 00277; 00278, (2015/06/11)

The present invention relates to quinazoline compounds of formula I that function as inhibitors of RET (rearranged during transfection) kinase enzyme activity: (Formula (I)) wherein X, R1, R2, R3, R4, R5, R6 and R7 are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions in which RET kinase activity is implicated.

4-Substituted quinazoline derivatives as novel EphA2 receptor tyrosine kinase inhibitors

Lim, Chae Jo,Oh, Kwang-Seok,Ha, Jae Du,Lee, Jeong Hyun,Seo, Ho Won,Chae, Chong Hack,Kim, Dae-Ghon,Lee, Mi-Jin,Lee, Byung Ho

, p. 4080 - 4083 (2014/09/29)

Erythropoietin-producing hepatocellular receptor tyrosine kinase subtype A2 (EphA2) is an attractive therapeutic target for suppressing tumor progression. In our efforts to discover novel small molecules to inhibit EphA2, a class of compound based on 4-substituted quinazoline containing 7-(morpholin-2-ylmethoxy) group was identified as a novel hit by high throughput screening campaign. Structural modification of parent quinazoline scaffolds by introducing substituents on aniline displayed potent inhibitory activities toward EphA2.

Fluorine-containing 6,7-dialkoxybiaryl-based inhibitors for phosphodiesterase 10 A: Synthesis and in vitro evaluation of inhibitory potency, selectivity, and metabolism

Schwan, Gregor,Barbar Asskar, Ghadir,Hoefgen, Norbert,Kubicova, Lenka,Funke, Uta,Egerland, Ute,Zahn, Michael,Nieber, Karen,Scheunemann, Matthias,Straeter, Norbert,Brust, Peter,Briel, Detlef

, p. 1476 - 1487 (2014/07/21)

Based on the potent phosphodiesterase 10 A (PDE10A) inhibitor PQ-10, we synthesized 32 derivatives to determine relationships between their molecular structure and binding properties. Their roles as potential positron emission tomography (PET) ligands were evaluated, as well as their inhibitory potency toward PDE10A and other PDEs, and their metabolic stability was determined in vitro. According to our findings, halo-alkyl substituents at position 2 of the quinazoline moiety and/or halo-alkyloxy substituents at positions 6 or 7 affect not only the compounds′ affinity, but also their selectivity toward PDE10A. As a result of substituting the methoxy group for a monofluoroethoxy or difluoroethoxy group at position 6 of the quinazoline ring, the selectivity for PDE10A over PDE3A increased. The same result was obtained by 6,7-difluoride substitution on the quinoxaline moiety. Finally, fluorinated compounds (R)-7-(fluoromethoxy)-6-methoxy-4-(3-(quinoxaline-2-yloxy)pyrrolidine-1-yl) quinazoline (16 a), 19 a-d, (R)-tert-butyl-3-(6-fluoroquinoxalin-2-yloxy) pyrrolidine-1-carboxylate (29), and 35 (IC50 PDE10A 11-65 nM) showed the highest inhibitory potential. Further, fluoroethoxy substitution at position 7 of the quinazoline ring improved metabolic stability over that of the lead structure PQ-10. Fluor your health: Phosphodiesterase 10 A (PDE10A) has emerged as an attractive target for the development of 18F-labelled brain imaging agents for positron emission tomography. A series of fluorinated dialkoxybiaryl compounds were synthesized and evaluated as PDE10A inhibitors, assisted by QSAR docking studies. The 7-fluoromethoxy derivative appears to be a promising candidate for further development.

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