Category: 1158763-55-3

In 2017,Molecules included an article by Xu, Shan; Sun, Chengyu; Chen, Chen; Zheng, Pengwu; Zhou, Yong; Zhou, Hongying; Zhu, Wufu. Application of 1158763-55-3. The article was titled 《Synthesis and biological evaluation of novel 8-morpholinoimidazo[1,2-a]pyrazine derivatives bearing phenylpyridine/phenylpyrimidine-carboxamides》. The information in the text is summarized as follows:

Three series of novel 8-morpholinoimidazo[1,2-a]pyrazine derivatives bearing phenylpyridine/phenylpyrimidine-carboxamides I [R = H, 4-Me, 3-F, etc.], II and III [R1 = H, 4-Me, 4-OMe, etc.] were designed and synthesized. All the compounds were evaluated for their IC50 values against three cancer cell lines (A549, PC-3 and MCF-7). Most of the target compounds exhibited moderate cytotoxicity against the three cancer cell lines. Two selected compounds III [R1 = 4-Me, 4-OMe] were further tested for their activity against PI3Kα kinase, and the results indicated that compound III [R1 = 4-OMe] showed inhibitory activity against PI3Kα kinase with an IC50 value of 1.25 μM. Structure-activity relationships (SARs) and pharmacol. results indicated that the replacement of the thiopyranopyrimidine with an imidazopyrazine was beneficial for the activity and the position of aryl group had a significant influence to the activity of these compounds The compounds II in which an aryl group substituted at the C-4 position of the pyridine ring were more active than I substituted at the C-5 position. Moreover, the cytotoxicity of compounds III bearing phenylpyrimidine-carboxamides was better than that of the compounds I and II bearing phenylpyridine-carboxamides. Furthermore, the substituents on the benzene ring also had a significant impact on the cytotoxicity and the pharmacol. results showed that electron donating groups were beneficial to the cytotoxicity. The results came from multiple reactions, including the reaction of 5-(3-Fluorophenyl)picolinic acid(cas: 1158763-55-3Application of 1158763-55-3)

5-(3-Fluorophenyl)picolinic acid(cas: 1158763-55-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Application of 1158763-55-3 Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Wu, Chunjiang; Xu, Shan; Guo, Yuping; Wu, Jielian; Luo, Rong; Wang, Wenhui; Tu, Yuanbiao; Le Chen; Zhu, Wufu; Zheng, Pengwu published an article on February 28 ,2018. The article was titled 《Design, synthesis and biological evaluation of phenylpicolinamide sorafenib derivatives as antitumor agents》, and you may find the article in Medicinal Chemistry Research.HPLC of Formula: 1158763-55-3 The information in the text is summarized as follows:

Two series of phenylpicolinamide sorafenib derivatives (14a-k, 15a-k) were designed and synthesized. They were evaluated for IC50 values against three cancer cell lines (A549, Hela, and MCF-7) and VEGFR2/KDR, BRAF, and CRAF kinases. Fourteen target compounds showed moderate to excellent cytotoxicity activity against the different cancer cells with potency from the single-digit μM to nanomole range. What’s more, six of them were equal to more potent than sorafenib against one or more cell lines. Most of the compounds showed bad activity against VEGFR2/KDR, BRAF, or CRAF kinases. The most promising compound 15f showed strong antitumor activities against A549 and MCF-7 cell lines with IC50 values of 5.43 ± 0.74 and 0.62 ± 0.21 μM, which were 1.29-6.79-fold more active than sorafenib (6.53 ± 0.82, 4.21 ± 0.62 μM), resp. and it exhibited moderate IC50 (7.1 μM) than 14f (IC50 = 3.1 μM). Structure-activity relationships (SARs) and docking studies indicated that replacement of diarylurea of sorafenib with phenylpicolinamide moiety benefits to the activity. The position of aryl group and the substitutions of aryl group have a great influence on antitumor activity and selectivity. Small volume groups of aryl group such as (substituted) alkyl groups (-CH3, -CF3), halogen atoms (-F) were favorable to the cytotoxicity. Exact action mechanism of target compounds is not quite clear and further study will be carried out to identify the target in near future. After reading the article, we found that the author used 5-(3-Fluorophenyl)picolinic acid(cas: 1158763-55-3HPLC of Formula: 1158763-55-3)

5-(3-Fluorophenyl)picolinic acid(cas: 1158763-55-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. HPLC of Formula: 1158763-55-3The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

SDS of cas: 1158763-55-3On March 31, 2017, Wang, Min; Wu, Chunjiang; Xu, Shan; Zhu, Yan; Li, Wei; Zheng, Pengwu; Zhu, Wufu published an article in Medicinal Chemistry (Sharjah, United Arab Emirates). The article was 《Synthesis, Biological Evaluation and Docking Studies of Sorafenib Derivatives N-(3-fluoro-4-(pyridin-4-yloxy)phenyl)-4(5)-phenylpicolinamides》. The article mentions the following:

Sorafenib is an important VEGFR2/KDR inhibitor which is widely used for the treatment of cancer. In this paper, two series of sorafenib analogs N-(3-fluoro-4-(pyridin-4-yloxy)phenyl)-4- phenylpicolinamides(13a-k) and N-(3-fluoro-4-(pyridin-4-yloxy)phenyl)-5-phenylpicolinamides (14a-k) were designed and synthesized. Their structures were confirmed by various anal. methods, such as 1 H and 13 C NMR, m.p., MS, HRMS. All of them were evaluated for IC50 values against three cancer cell lines (A549, PC-3 and MCF-7). Eleven of the synthesized compounds showed moderate to excellent cytotoxicity activity against different cancer cells, whose potency from single-digit μM to nanomolar range. And five of them were equal to more potent than sorafenib against one or more cell lines. The most promising compound 14c showed excellent antitumor activities against PC-3 and MCF-7 cell lines with IC50 values of 2.62±1.07 μM and 1.14±0.92 μM, which were 1.15 to 2.75-fold more active than sorafenib (3.03±1.01 μM, 3.14±1.65 μM), resp. Structure-activity relationships (SARs) and docking studies indicated that the replacement of diarylurea of sorafenib with phenylpicolinamide moiety benefited to the activity. The position of aryl group and the substituents of aryl group had a great influence on antitumor activity and selectivity. The aryl groups with the substitute of alkyl groups (-CH3), halogen atoms (-F,Cl) were favorable to the cytotoxicity. However, this series of compounds showed moderate activity against VEGFR2/KDR kinase. Mechanism of target compounds was not quite clear and further study will be carried out to identify the possible target.5-(3-Fluorophenyl)picolinic acid(cas: 1158763-55-3SDS of cas: 1158763-55-3) was used in this study.

5-(3-Fluorophenyl)picolinic acid(cas: 1158763-55-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. SDS of cas: 1158763-55-3The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem