Tag: 100-200

Ligustrazine derivatives. Part 6: design, synthesis and evaluation of novel ligustrazinyl acylguanidine derivatives as potential cardiovascular agents was written by Li, Zhenyu;Yu, Fang;Cui, Lei;Zhan, Peng;Wang, Shouxun;Shen, Yuemao;Liu, Xinyong. And the article was included in Medicinal Chemistry in 2012.Computed Properties of C8H12N2O This article mentions the following:

A series of novel Ligustrazinyl acylguanidines I [R = H, Me, C₆H₄Me-4, C₆H₄OMe-4, CH₂C₆H₄F-4, CH₂C₆H₄Cl-3, CH₂C₆H₄OMe-4, CH₂C₆H₄F-2, CH₂C₆H₄Cl-2, CH₂Ph, CH₂C₆H₃Cl₂-2,4, CH₂C₆H₃Cl₂-3,4, 3,5,6-trimethylpyrazin-2-yl] was designed, synthesized and evaluated for their protective effect on injured vascular endothelial cell (ECV-304). The preliminary results demonstrated that some compounds possessed more potent activities than that of Ligustrazine in stimulating replication of the injured endothelial cell. Among the active compounds, compounds I [R = Me, CH₂C₆H₄Cl-3, CH₂C₆H₃Cl₂-3,4] displayed remarkable antioxidative activity with low EC₅₀ values of 0.097, 0.059 and 0.094 mM, resp. 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. A number of pyrazine-based derivatives were used as dyes or fluorescent probes.Computed Properties of C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Design, synthesis and evaluation of novel chloro-oxime derivatives for neurodegenerative diseases was written by Zhang, Aijun;Fu, Pengfei;Zhang, Zaijun;Chen, Haiyun;Yu, Pei. And the article was included in Journal of Pharmaceutical and Biomedical Sciences in 2016.Synthetic Route of C8H12N2O This article mentions the following:

Neurodegenerative disease is a fatal disease of the human nervous system, including Alzheimer’s disease, Parkinson’s disease, Huntington’s disease, amyotrophic lateral sclerosis and related polyglutamine expansion diseases. The US FDA had approved several drugs to treat neurodegenerative diseases, however, almost none of them could delay progress of these diseases and offer cure. A key mol. pathway implicated in neurodegenerative diseases is the misfolding aggregation and accumulation of proteins in neurons. Chloro-oxime derivatives, such as bimoclomol and arimoclomol, promote the expression of heat shock proteins and improve the abilities of normal protein folding and degrade misfolded proteins. Based on the structure of bimoclomol and arimoclomol, we substituted the pyridine and piperazine by TMP and other amino groups, and synthesized a series of novel chloro-oxime derivatives Among these chloro-oxime derivatives, compounds 9b and 13b were demonstrated to be neuroprotective against MG-132-induced neurotoxicity in SH-SY5Y cells. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Synthetic Route 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. 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.Synthetic Route of C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

[2.2](2,6)- and [2.2](2,5)Pyrazinophanes: synthesis and molecular structure was written by Eiermann, Uwe;Krieger, Claus;Neugebauer, Franz A.;Staab, Heinz A.. And the article was included in Chemische Berichte in 1990.Formula: C8H12N2O This article mentions the following:

The title compounds I, ,II and III and their Me derivatives were synthesized either by photolytic sulfur extrusion from the corresponding 2,11-dithia[3.3]pyrazinophanes or by Hofmann 1,6-elimination of the appropriate [(5-methyl-2-pyrazinyl)methyl]trimethylammonium hydroxides followed by dimerization of the generated 2,5-dihydro-2,5-bis(methylene)pyrazines. α-Chlorination of the methylpyrazines with N-chlorosuccinimide gave the required precursors. The results of the x-ray structure determinations for the title compounds which indicate an unequivocal isomer assignment are discussed with regard to steric strain in these mols. The electronic spectra of the title compounds are reported and compared with those of the parent methylpyrazines. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Formula: C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazinesare six-membered aromatic heterocyclic organic compounds with two nitrogen atoms at 1,4-positions. Pyrazine is a weaker base (pKb = 13.4) than pyridine (pKb = 8.8), pyrimidine (pKb = 12.7). Pyrazine-based skeletons were incorporated into agents targeting a range of ailments. Many derivatives were synthesized and evaluated as potential cancer treatments.Formula: C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reduction of azanaphthalenes by sodium borohydride in trifluoroacetic acid was written by Bugle, Robert C.;Osteryoung, Robert A.. And the article was included in Journal of Organic Chemistry in 1979.Category: pyrazines This article mentions the following:

Azanaphthalenes were reduced in high yield to the corresponding amines by tris(trifluoroacetoxy)borohydride. The pyrazine ring can be preferentially reduced within a mixed heteroaromatic nucleus, resulting in the regiospecific and clean reduction of many azanaphthalenes. A convenient one-step preparation of both tetrahydropteridines I and II is discussed, in addition to the preparation of 1,2,3,4-tetrahydroquinoxaline. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3Category: pyrazines).

Pyrido[2,3-b]pyrazine (cas: 322-46-3) 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. A large number of pyrazine derivatives are known for their antitumor, antibiotic, anticonvulsant, antituberculosis, and diuretic activities.Category: pyrazines

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Infrared spectra of heterocyclic compounds. IV. Infrared spectra of monosubstituted pyridine derivatives was written by Shindo, Hideyo. And the article was included in Pharmaceutical Bulletin in 1957.Recommanded Product: Ethyl pyrazine-2-carboxylate This article mentions the following:

The infrared spectra were determined and the maximum frequencies tabulated for 2-, 3-, and 4-substituted pyridines, in which the substituents were NO₂, CN, Ac, CHO, CO₂Et, CONH₂, Br or Cl, C₅H₄N, Me, Et, MeO, and NH₂ (38 compounds). All the compounds were prepared by well-known methods: reduction of the corresponding N-oxides gave the 4-O₂N (m. 50°), 4-Cl (picrate, m. 144°), and 4-MeO (b₃₀ 92-4°) derivatives; perhydrol oxidation of the corresponding H₂N derivatives gave the 3- and 2-O₂N derivatives (m. 55° and 71°, resp.); ester condensation of the corresponding EtO₂C derivatives gave the 2- and 3-Ac derivatives (b. 190° and 220°, resp.); and the Gattermann reaction on 3-H₂N derivative gave the 3-Cl and 3-Br derivatives (b. 148-9° and 172-3°, resp.). The previously described exptl. method (C.A. 51, 5557b) for the infrared determinations was used. Results were discussed in their bearing on (1) the ring CH out-of-plane bending vibrations, which are in the region 700-900 cm.^-1 and can be interpreted as analogous to the corresponding substituted benzenes, (2) the ring double-bond stretching vibrations, which show 2 bands between 1550 and 1620 cm.^-1 that are directly related to the type of π-electron distribution on the ring, and (3) the electronic effect of ring N, which is shown as a frequency shift in the absorption of the substituent dependent upon its position in the ring. A series of weak absorptions at 990-1220 cm.^-1 was found to be very characteristic for the type of substitution. The linear correlations between the frequencies and σ-values of the substituents in benzene derivatives could be extended to these pyridine derivatives by using the σ-values of 0.93, 0.62, and 1.02, resp., for 4-, 3-, and 2-positions. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Recommanded Product: Ethyl pyrazine-2-carboxylate).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) 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 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.Recommanded Product: Ethyl pyrazine-2-carboxylate

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis and biological evaluation of new tetramethylpyrazine-based chalcone derivatives as potential anti-Alzheimer agents was written by Wang, Meng;Qin, Hua-Li;Leng, Jing;Ameeduzzafar;Amjad, Muhammad Wahab;Raja, Maria Abdul Ghafoor;Hussain, Muhammad Ajaz;Bukhari, Syed Nasir Abbas. And the article was included in Chemical Biology & Drug Design in 2018.Application In Synthesis of (3,5,6-Trimethylpyrazin-2-yl)methanol This article mentions the following:

In the current study, a series of new ligustrazine-based chalcones was synthesized. For insertion of tetramethylpyrazine (TMP, also designated as ligustrazine) in chem. backbone of chalcone, a new ligustrazine-based aldehyde was prepared New ketones were synthesized for inclusion of quinazolin-4-yl amino and pyrazin-2-yl amino moieties. The newly synthesized compounds were screened for acetylcholinesterase, butyrylcholinesterase, and monoamine oxidases (MAO) inhibitory activities and also for in vitro cytotoxicity on PC12 cells. The effect of these compounds against amyloid β-induced cytotoxicity and aggregation was also investigated. The synthesized compounds effectively inhibited the related enzymes and also exhibited neuroprotective effects. Most of the compounds displayed better inhibitory potencies against Aβ aggregation than reference compounds Some compounds such as 11e and 16b showed very potent effects on multiple targets exhibiting behavior as multifunctional anti-Alzheimer agents. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Application In Synthesis 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.Application In Synthesis of (3,5,6-Trimethylpyrazin-2-yl)methanol

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

General Method for the Amination of Aryl Halides with Primary and Secondary Alkyl Amines via Nickel Photocatalysis was written by Song, Geyang;Nong, Ding-Zhan;Li, Jing-Sheng;Li, Gang;Zhang, Wei;Cao, Rui;Wang, Chao;Xiao, Jianliang;Xue, Dong. And the article was included in Journal of Organic Chemistry in 2022.Application of 912773-21-8 This article mentions the following:

It was reported that Ni(II)-bipyridine complex catalyzed efficient C-N coupling of aryl chlorides and bromides with various primary and secondary alkyl amines under direct excitation with light. Intramol. C-N coupling was also demonstrated. The feasibility and applicability of the protocol in organic synthesis was attested by more than 200 examples. In the experiment, the researchers used many compounds, for example, 2-Bromo-5-chloropyrazine (cas: 912773-21-8Application of 912773-21-8).

2-Bromo-5-chloropyrazine (cas: 912773-21-8) 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.Application of 912773-21-8

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Liquid chromatography-mass spectrometry method for determination of tetramethylpyrazine and its metabolite in dog plasma was written by Wang, Peng;Jin, Xin;Qi, Meiling;Fang, Lin. And the article was included in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences in 2004.Product Details of 75907-74-3 This article mentions the following:

A liquid chromatog.-mass spectrometry method is described for the determination of tetramethylpyrazine (TMP) and its active metabolite, 2-hydroxymethyl-3,5,6-trimethylpyrazine (HTMP) in dog plasma. This method involves a plasma clean-up step using protein precipitation procedure followed by LC separation and pos. electrospray ionization mass spectrometry detection (ESI-MS). Chromatog. separation of the analytes was achieved on a C18 column using a mobile phase of methanol, water and acetic acid (50:50:0.6, volume/volume/v) at a flow rate of 1.0 mL/min. Selected ion monitoring (SIM) mode was used for analyte quantitation at m/z 137.2 for TMP, m/z 153.2 for HTMP and m/z 195.2 for caffeine. The linearity was obtained over the concentration ranges of 20-6000 ng/mL for TMP and 20-4000 ng/mL for HTMP and the lower limit of quantitation was 20 ng/mL for both analytes. For each level of QC samples, both inter- and intraday precisions (R.S.D.) were ≤7.4% for TMP and ≤6.0% for HTMP, and accuracy (R.E.) was ±6.0% for TMP and ≤3.5% for HTMP. The proposed LC-MS method was successfully applied to the pharmacokinetic studies of a TMP formulation preparation after oral administration to beagle dogs. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Product Details of 75907-74-3).

(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 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.Product Details of 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Substituent-directing effects in the homolytic acylation of pyrazine derivatives was written by Houminer, Y.;Southwick, E. W.;Williams, D. L.. And the article was included in Journal of Organic Chemistry in 1989.COA of Formula: C7H8N2O2 This article mentions the following:

The homolytic acylation of various monosubstituted pyrazines was studied for a wide spectrum of substituents. MeO and Cl substituents directed ortho to yield the corresponding 2,3-disbustituted pyrazines. Ac, CO₂Et, and CONH₂ groups directed para, leading to the corresponding 2,5-disubstituted pyrazines. These selectivities result from the combination of the inductive and resonance effects of the substituents. The synthetic potential of the acylation reaction is demonstrated in the preparation of some novel pyrazine flavorants, e.g., I. Thus, 2-chloropyrazine was treated with Me₂CHCHO, Me₃COOH, FeSO₄, and H₂SO₄ in H₂O to give (chloropyrazinyl)methylpropanone II. Treating furfuryl mercaptan with NaOEt and then II in EtOH gave 32% I. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1COA of Formula: C7H8N2O2).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) 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. Substituted pyrazines have been found as subunits of multiple synthetically constructed therapeutic agents, as well as several natural products.COA of Formula: C7H8N2O2

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Pyrazinoates as antiparasitic agents against Trypanosoma cruzi was written by Vasconcelos, Camilla I.;Varela, Marina T.;Torrecilhas, Ana C.;Fernandes, Joao P. S.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2018.Formula: C7H8N2O2 This article mentions the following:

This work reports a repurposing study of pyrazinoic acid (1) and Me (2), Et (3) and 2-chloroethyl (4) ester derivatives with antimycobacterial activity, in assays against Trypanosoma cruzi. The compounds and benznidazole, the standard antitrypanosoma drug, were evaluated in concentrations ranging from 100 to 6.25 μg/mL. The results showed that compounds 2 and 3 (EC₅₀ = 182 and 447 μM) significantly reduced the infection rate of the parasite into the mammalian cells at 100 μg/mL (p < 0.05) in a similar way to benznidazole. In addition, all the compounds also significantly reduced the number of intracellular parasites (compound 1 at 50 μg/mL, and compounds 2-4 at 100 μg/mL, p < 0.05) in comparison to the control. Compounds 1 and 2 were more effective than benznidazole at 50 μg/mL (p < 0.001). Moreover, compounds 1-4 did not show significant cytotoxicity against THP-1, J774, and HeLa cells (>1000 μM), indicating that they possess considerable selectivity against the parasites. This report represents the first study of such compounds against T. cruzi, indicating the potential of pyrazinoates as antiparasitic agents. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Formula: C7H8N2O2).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) 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.Formula: C7H8N2O2

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem