Category: 75907-74-3

Synthesis and biological evaluation of novel ligustrazine-chalcone derivatives as potential anti-triple negative breast cancer agents was written by Luo, Yingqi;Wu, Wenhao;Zha, Dailong;Zhou, Wenmin;Wang, Chengxu;Huang, Jianan;Chen, Shaobin;Yu, Lihong;Li, Yuanzhi;Huang, Qinghui;Zhang, Jianye;Zhang, Chao. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2021.Category: pyrazines This article mentions the following:

A series of novel ligustrazine-chalcone hybrids I [R = H, 4-F, 3,5-(MeO)₂, etc.] was synthesized and evaluated for their in vitro and in vivo antitumor activities. The results showed that most of these compounds exhibited significant in vitro cytotoxicity against MDA-MB-231, MCF-7, A549 and HepG2 cell lines with IC₅₀ values as low as sub-micromole. Among them, compounds I [R = 4-MeO, 4-F] possessed better comprehensive characteristics for antiproliferation effects on both MDA-MB-231 (IC₅₀: compound I [R = 4-MeO], 1.60 鍗?0.21娓璏; compound I [R = 4-F], 1.67 鍗?1.25娓璏) and MCF-7 (IC₅₀: compound I [R = 4-MeO], 1.41 鍗?0.23娓璏; compound I [R = 4-F], 1.54 鍗?0.30娓璏). They also exhibited potent colony-formation inhibitory abilities on above two cell lines in both concentration and time dependent manners, as well as significantly suppression capabilities against migration of such cell lines in a concentration dependent manner by wound-healing assay. Of note, compound I [R = 4-MeO] could significantly induce apoptosis of MDA-MB-231 cells in a concentration dependent manner and inhibited transformation of growth cycle of MDA-MB-231 cells and blocked cell growth cycle in G0/G1 phase. Moreover, in vivo antiproliferation assay of compound I [R = 4-MeO] on TNBC model indicated such compound had a remarkable potency against tumor growth with a widely safety window. Further immunohistochem. anal. illustrated that compound I [R = 4-MeO] was provided with a potent capacity to significantly reduce Ki-67 pos. rate in a dose dependent manner. All results suggested that these hybrids presented both in vitro and in vivo proliferation inhibition potency against breast cancer and further development with good therapeutic potential should be of great interest. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Category: pyrazines).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine derivatives have antitumor, antibiotic, anticonvulsant, antituberculous and diuretic effects as well as kinase, enzymatic and potent tubulin and FtsZ polymerization inhibitory activities. Pyrazine and a variety of alkylpyrazines are flavor and aroma compounds found in baked and roasted goods. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human Granulocytes.Category: pyrazines

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Novel homo-bivalent and polyvalent compounds based on ligustrazine and heterocyclic ring as anticancer agents was written by Wang, Jiawen;Hong, Ge;Li, Guoliang;Wang, Wenzhi;Liu, Tianjun. And the article was included in Molecules in 2019.Related Products of 75907-74-3 This article mentions the following:

Bivalent and polyvalent inhibitors can be used as antitumor agents. In this experiment, eight ligustrazine dimers and seven ligustrazine tetramers linked by alkane diamine with different lengths of carbon chain lengths were synthesized. After screening their antiproliferation activities against five cancer cell lines, most ligustrazine derivatives showed better cytotoxicity than the ligustrazine monomer. In particular, ligustrazine dimer 8e linked with decane-1,10-diamine exhibited the highest cytotoxicity in FaDu cells with an IC50 (50% inhibiting concentration) value of 1.36 nM. Further mechanism studies suggested that 8e could induce apoptosis of FaDu cells through the depolarization of mitochondrial membrane potential and S-phase cell cycle arrest. Inspired by these results, twenty-seven addnl. small mol. heterocyclic dimers linked with decane-1,10-diamine and nine cinnamic acid dimers bearing ether chain were synthesized and screened. Most monocyclic and bicyclic aromatic systems showed highly selective anti-proliferation activity to FaDu cells and low toxicity to normal MCF 10A cells. The structure-activity relationship revealed that the two terminal amide bonds and the alkyl linker with a chain length of 8-12 carbon were two important factors to maintain its antitumor activity. In addition, the ADMET calculation predicted that most of the potent compounds had good oral bioavailability. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Related Products of 75907-74-3).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazines are part of several biologically active polycyclic compounds; examples are quinoxalines, phenazines; and the bio-luminescent natural products pteridines, flavins, and their derivatives. Pyrazine and a variety of alkylpyrazines are flavor and aroma compounds found in baked and roasted goods. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human Granulocytes.Related Products of 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Identification of hydroxymethylpyrazines using mass spectrometry was written by Bohman, Bjoern;Flematti, Gavin R.;Barrow, Russell A.. And the article was included in Journal of Mass Spectrometry in 2015.Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol This article mentions the following:

Pyrazines are well-known natural products that are present in bacterial odors and food flavoring agents and are used as insect pheromones. Recently, a number of hydroxymethylpyrazines have been identified as thynnine wasp pheromones and orchid semiochems. that are essential for pollination in sexually deceptive plants. These compounds are present in low amounts in complex blends, making GC-MS (including high-resolution techniques) the method of choice for their structure elucidation. We report the EI mass spectra for 14 representative compounds and have found that based on characteristic fragmentations, it is possible to distinguish between different positional isomers of hydroxymethylpyrazines. The presence or absence of either [M – 17]⁺, [M – 18]^{+璺?/sup> or [M – 19]+ fragment species provides characteristic information to allow the distinction between the different isomers. Considering the importance of pyrazines as a group of bioactive natural products, and the recent findings of biol. activity for hydroxymethylpyrazines, our results presented here will aid the identification of these compounds in other biol. systems. Copyright 婕?2015 John Wiley & Sons, Ltd. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol).}

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. Pyrazine and a variety of alkylpyrazines are flavor and aroma compounds found in baked and roasted goods. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human Granulocytes.Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Design, synthesis and biological evaluation of thrombin inhibitors with 1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine nucleus was written by Chen, Dongxing;Shi, Jinyu;Chen, Qiufang;Zhang, Rui;Gong, Guoqing;Xu, Yungen;Zhu, Qihua. And the article was included in Gaodeng Xuexiao Huaxue Xuebao in 2017.HPLC of Formula: 75907-74-3 This article mentions the following:

Compound 1, a new thrombin inhibitor with 1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine nucleus, was selected as lead compound, and fourteen carbamate derivatives derivatives were designed and prepared Furthermore, a twin drug (11) was synthesized by coupling compound 1 with 2-hydroxymethyl-3,5,6-trimethylpyrazine (HTMP). The structures of all the target compounds were confirmed by ¹H-NMR, ¹³C-NMR and HRMS. Preliminary biol. activity test results indicated that all of the tested compounds exhibited a certain degree of inhibitory effect on thrombin-induced platelet aggregation, among which compound 4b [IC₅₀ = (0.11鍗?.08) 娓璵ol/L] showed better anti-platelet aggregation activity than dabigatran etexilate [IC₅₀ = (0.60鍗?.05) 娓璵ol/L]. The in vitro exptl. results in rat venous thrombosis model demonstrated compound 4b could significantly reduce thrombosis in a dose-response manner. Compound 11, which showed weak inhibitory effect on thrombin-induced platelet aggregation, also displayed comparable inhibitory effect on rat venous thrombosis with dabigatran etexilate. The study pointed out that the enhanced potency of compound 11 may be the synergetic effect on HTMP and compound 1 which were generated by hydrolysis in vivo. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3HPLC of Formula: 75907-74-3).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine is an N-heterocyclic moiety, and it can be easily prepared from ethylenediamine and 1,2-diketone, 浼?hydroxyketone, 浼?methyl ketone. A number of pyrazine-based derivatives were used as dyes or fluorescent probes.HPLC of Formula: 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Design, synthesis, and biological activities of novel Ligustrazine derivatives was written by Cheng, Xian-Chao;Liu, Xin-Yong;Xu, Wen-Fang;Guo, Xiu-Li;Ou, Yang. And the article was included in Bioorganic & Medicinal Chemistry in 2007.Computed Properties of C8H12N2O This article mentions the following:

A series of novel Ligustrazine derivatives was designed, synthesized, and assayed for their protective effects on damaged ECV-304 cells and antiplatelet aggregation activities. The results showed that most Ligustrazine derivatives exhibited lower EC₅₀ values for protective effects on the ECV-304 cells damaged by hydrogen peroxide in comparison with Ligustrazine. And some Ligustrazine derivatives presented better antiplatelet aggregation activities than Ligustrazine. The derivatives containing the bisphenylmethyl pharmacophore (7a-c) exhibited highest potency. Compound 7a displayed most potential protective effects on the ECV-304 cells damaged by hydrogen peroxide, and compound 7c was found to be the most active antiplatelet aggregation agent. Structure-activity relationships were briefly discussed. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Computed Properties of C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine heterocycles and their benzo derivatives possess many interesting properties, including chemical reactivity profiles, and have diverse applications in total synthesis, medicine, chemical biology, materials, dyes, and imaging. Pyrazine-based skeletons were incorporated into agents targeting a range of ailments. Many derivatives were synthesized and evaluated as potential cancer treatments.Computed Properties of C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Intramolecular Diels-Alder reaction of pyrazines with an alkenyl side chain was written by Chen, Bin;Yang, Chu-Yao;Ye, De-Yong. And the article was included in Tetrahedron Letters in 1996.Electric Literature of C8H12N2O This article mentions the following:

Intramol. Diels-Alder reaction of a series of pyrazines bearing a 5-membered-ω-alkene side chain, I (X = O, SO, SO₂, S), in refluxing trifluoroacetic acid led to the formation of bridged tricyclic compounds II. These cycloadducts underwent retro Diels-Alder reaction in refluxing nitrobenzene to give the original pyrazines. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Electric Literature of C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine has the elements of symmetry for the point group D2h. It has three mutually perpendicular two-fold axes. It also has three mutually perpendicular planes of symmetry. As a result, pyrazine also has a centre of symmetry. Substituted pyrazines have been found as subunits of multiple synthetically constructed therapeutic agents, as well as several natural products.Electric Literature of C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis of tetramethylpyrazine metabolites was written by Liu, Xinyong;Ge, Weiying;Xu, Lijun;Zhang, Junren;Wang, Haiyan;Pan, Shuju. And the article was included in Shandong Yike Daxue Xuebao in 1997.COA of Formula: C8H12N2O This article mentions the following:

2-Acetoxylmethyl-3,5,6-trimethylpyrazine, 3,5,6-trimethylpyrazine methanol and 3,5,6-trimethylpyrazine formic acid were prepared from tetramethylpyrazine oxidation The alc. and the acid were tested active in lowering both cholesterol and LDL level in rabbit. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3COA of Formula: C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine heterocycles and their benzo derivatives possess many interesting properties, including chemical reactivity profiles, and have diverse applications in total synthesis, medicine, chemical biology, materials, dyes, and imaging. Pyrazines undergo nearly all of the same reactions as pyrimidines, from nucleophilic substitution (SNAr) to palladium-catalyzed cross coupling reactions.COA of Formula: C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis and protective effect of new ligustrazine-vanillic acid derivatives against CoCl₂-induced neurotoxicity in differentiated PC12 cells was written by Xu, Bing;Xu, Xin;Zhang, Chenze;Zhang, Yuzhong;Wu, GaoRong;Yan, Mengmeng;Jia, Menglu;Xie, Tianxin;Jia, Xiaohui;Wang, Penglong;Lei, Haimin. And the article was included in Chemistry Central Journal in 2017.Category: pyrazines This article mentions the following:

To develop new ligustrazine derivatives with neuroprotective effects, the synthesis of several ligustrazine-vanillic acid amide derivatives I [R = hydroxy, methylamino, 2-aminonaphthyl, etc.] and screened their protective effect on the injured PC12 cells damaged by CoCl₂. The results showed that most of the newly synthesized compounds I exhibited higher activity than ligustrazine, of which, compound I [R = 3-(dimethylamino)anilino] displayed the highest potency with EC₅₀ values of 17.39 ± 1.34 μM. Structure-activity relationships were studied. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Category: pyrazines).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazines are volatile compounds that are used in the cosmetic, food, flavor, and fragrance industries. Pyrazine heterocycles and their benzo derivatives possess many interesting properties, including chemical reactivity profiles, and have diverse applications in total synthesis, medicine, chemical biology, materials, dyes, and imaging.Category: pyrazines

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Design and synthesis of indobufen esters was written by Li, Feng;Wang, Jie;Li, Jia-ming;Zuo, Jian. And the article was included in Anhui Yiyao in 2015.Computed Properties of C8H12N2O This article mentions the following:

Indobufen was used as starting material, and three Indobufen esters were designed and synthesized based on association principle and prodrug principle of medicinal chem. The structures of the target compounds were characterized by IR, MS, ¹H NMR and ¹³C NMR. The anti-platelet aggregation activity of the target compounds is being tested in vitro. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Computed Properties of C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine derivatives have antitumor, antibiotic, anticonvulsant, antituberculous and diuretic effects as well as kinase, enzymatic and potent tubulin and FtsZ polymerization inhibitory activities. Pyrazines undergo nearly all of the same reactions as pyrimidines, from nucleophilic substitution (SNAr) to palladium-catalyzed cross coupling reactions.Computed Properties of C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

An unexpected replacement of a methyl with an amino in the tetramethylpyrazine system was written by Lang, Ming;Yao, Hui;Fu, Pengfei;Cai, Wei;Wang, Yuqiang;Yu, Pei. And the article was included in Research on Chemical Intermediates in 2015.Computed Properties of C8H12N2O This article mentions the following:

A novel and unexpected product, 5-amino-3,6-dimethyl-2-pyrazinecarbonitrile (3), was obtained during the attempted to synthesis of 3,5,6-trimethyl-2-pyrazinecarbonitrile (2) from its corresponding alc. (1) by the catalytic amount of KI or I₂ in combination with TBHP as an external oxidant. The product was confirmed by ESI-MS, HRMS, ¹H-NMR, ¹³C-NMR, and 2D-NMR. The mechanism for the formation of the amino group in the tetramethylpyrazine system is also proposed. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Computed Properties of C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazines are volatile compounds that are used in the cosmetic, food, flavor, and fragrance industries. A number of pyrazine-based derivatives were used as dyes or fluorescent probes.Computed Properties of C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem