Tag: 100-200

Synthesis and biological evaluation of pyrido[2,3-b]pyrazine and pyrido[2,3-b]pyrazine-N-oxide as selective glycine antagonists was written by Cugola, Alfredo;Donati, Daniele;Guarneri, M.;Micheli, Fabrizio;Missio, Andrea;Pecunioso, Angelo;Reggiani, Angelo;Tarzia, G.;Zanirato, V.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1996.Synthetic Route of C7H5N3 This article mentions the following:

Pyrido[2,3-b]pyrazines and pyrido[2,3-b]pyrazines-N-oxides have been synthesized and evaluated for in vitro/in vivo antagonistic activity at the glycine site on the NMDA receptor. Efforts to improve the glycine vs. AMPA selectivity focussed on both aromatic substitution and on modification of the heterocyclic ring. The compounds showed a good affinity for the glycine binding site and > 100-fold selectivity vs. the AMPA receptor. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3Synthetic Route of C7H5N3).

Pyrido[2,3-b]pyrazine (cas: 322-46-3) belongs to pyrazine derivatives. Pyrazine is an N-heterocyclic moiety, and it can be easily prepared from ethylenediamine and 1,2-diketone, α-hydroxyketone, α-methyl ketone. Pyrazines undergo nearly all of the same reactions as pyrimidines, from nucleophilic substitution (SNAr) to palladium-catalyzed cross coupling reactions.Synthetic Route of C7H5N3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Development of 2-hydroxymethyl-3,5,6-trimethylpyrazine palmitate-loaded lipid emulsion: formulation, optimization, characterization, pharmacokinetics, biodistribution and pharmacodynamics was written by Cao, Ran;Li, Qian;Li, Hui;Chu, Ting;Jin, Hui;Mao, Sheng-jun. And the article was included in Journal of Drug Targeting in 2013.SDS of cas: 75907-74-3 This article mentions the following:

Tetramethylpyrazine (TMP) is used to treat cerebrovascular and cardiovascular diseases. However, it displays a short half-life that restricts clin. applications. 2-Hydroxymethyl-3,5,6-trimethylpyrazine (HTMP) is the principal active metabolite of TMP, with similar activity of TMP. Therefore, it makes sense to improve the biopharmaceutical characteristics via HTMP bypassing TMP. Purpose: To prolong the half-life of HTMP and achieve improved bioavailability and efficacy compared to com. available product of tetramethylpyrazine phosphate injection (TMPP-I). A lipophilic prodrug of HTMP, palmitate of HTMP (HTMPP) was synthesized, and then the lipid emulsion of HTMPP was developed. The middle cerebral artery occlusion (MCAO) model was applied to evaluate the efficacy in different administration group. The optimized formulation consisted of 1.5% (w/v) HTMPP, 15% (w/v) soybean oil, 1.2% (w/v) soybean lecithin and 0.3% (w/v) poloxamer 188. The AUC_0-180 min and the half-life of HTMP in HTMPP-LE was 2.05-fold and 1.48-fold greater than that in TMPP-I. The brain AUC_0-120 min of HTMP in HTMPP-LE group increased by 145.6% compared to that in TMPP-I group. These differences could be primarily attributed to dissimilar metabolism between HTMPP and TMP. Consistently, HTMPP-LE exhibited better efficacy on ischemia/reperfusion model than TMPP-I. The developed HTMPP-LE suggests a great therapeutic potential for clin. applications. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3SDS of cas: 75907-74-3).

(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). Pyrazines are chemical compounds (technically called “methoxypyrazines”) found in grape skin and stems that are responsible for many “green” flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.SDS of cas: 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Preparation of polystyryl-1,5-naphthyridine, polystyrylpyrido[2,3-b]pyrazine, and some of their copper(II) complexes was written by Valera, Nestor S.;Hendricker, David G.. And the article was included in Polymer in 1981.SDS of cas: 322-46-3 This article mentions the following:

Poly(styryl-1,5-naphthyridine) and poly(styrylpyrido[2,3-b]pyrazine) Cu (II) complexes were prepared by lithiation of brominated divinylbenzene-styrene copolymer, followed by addition of 1,5-naphthyridine or pyrido[2,3-b]pyrazine, resp. Cu(NO₃)₂ was added to the polystyryl compounds, and the resulting complexes were characterized by elemental anal. and IR. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3SDS of cas: 322-46-3).

Pyrido[2,3-b]pyrazine (cas: 322-46-3) 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. Substituted pyrazines have been found as subunits of multiple synthetically constructed therapeutic agents, as well as several natural products.SDS of cas: 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Hydrophobicity parameter of diazines. III. Relationship of partition coefficients of monosubstituted diazines and pyridines in different partitioning systems was written by Yamagami, Chisako;Takao, Narao;Fujita, Toshio. And the article was included in Journal of Pharmaceutical Sciences in 1993.SDS of cas: 6924-68-1 This article mentions the following:

The logarithm of the 1-octanol-water partition coefficient value (log P_oct) was compared with those from CHCl₃-water (log P_CL) and di-n-Bu ether-water (log P_E) for (di)azines substituted singly by nonhydrogen-bonding and hydrogen-accepting substituents (2-substituted pyrazines, 2-substituted pyrimidines, and 2-substituted pyridines). The difference between log P_oct and log P_CL for diazines was primarily governed by the number of hydrogen-bonding sites in the substituent. For 2-substituted pyridines, the difference in the hydrogen-bonding association of the ring N-atom with octanol from that with CHCl₃ was also significant. In the relationship between log P_oct and log P_E, the hydrogen-bonding solvations of the ring N-atom(s), as well as the hydrogen-accepting substituent with octanol, should be taken into account because the Bu ether acts as a nonhydrogen-bonding solvent. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1SDS of cas: 6924-68-1).

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

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Alkylating reduction of some polynitrogen heteroaromatic compounds was written by Cosmao, Jean Marie;Collignon, Noel;Queguiner, Guy. And the article was included in Journal of Heterocyclic Chemistry in 1979.Electric Literature of C7H5N3 This article mentions the following:

The reduction-alkylation of quinoxaline, phthalazine and pyrido[2,3-b]pyrazine by KBH₄ in a carboxylic acid medium is described. HCO₂H, HOAc, ClCH₂CO₂H, and EtCO₂H were used. The diazine ring of the mol. was reduced and alkylated into an N,N‘-dialkyltetrahydro compound With quinoxaline and HCO₂H, N-formylation may be an important factor. Sodium borodeuteride gave a hexadeuterated compound In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3Electric Literature of C7H5N3).

Pyrido[2,3-b]pyrazine (cas: 322-46-3) belongs to pyrazine derivatives. Pyrazine is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. Pyrazines are chemical compounds (technically called “methoxypyrazines”) found in grape skin and stems that are responsible for many “green” flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.Electric Literature of C7H5N3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Separation and characterization of chloroform-soluble preasphaltenes in non-distillable coal liquids was written by Allen, Todd W.;Hurtubise, Robert J.;Silver, Howard F.. And the article was included in Fuel in 1987.Computed Properties of C7H5N3 This article mentions the following:

N compounds and hydroxy-aromatics from CHCl₃-soluble/PhMe-insoluble preasphaltenes of a Kentucky coal-liquid sample were characterized by elemental anal., IR spectroscopy and field-ionization mass spectrometry. A similar approach was used for the general characterization of the pyridine-soluble/CHCl₃-insoluble preasphaltenes. A new HPLC method was applied for the separation of a N-compound fraction and a hydroxy-aromatic fraction from the CHCl₃-soluble/PhMe-insoluble preasphaltenes. The chromatog. method was very selective in separating polar N compounds and polar hydroxy-aromatics The separation order within a given fraction was based on increasing polarity of the compounds Spectral results indicated that the CHCl₃-soluble preasphaltenes were composed of structures with mol. weights ≈ 200-800 and were predominantly mono- and dihydroxy compounds In addition, nonhydroxy compounds that contained pyrrolic functionality were present. Solubility information for the preasphaltenes in various solvents was also obtained. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3Computed Properties of C7H5N3).

Pyrido[2,3-b]pyrazine (cas: 322-46-3) 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). Pyrazines undergo nearly all of the same reactions as pyrimidines, from nucleophilic substitution (SNAr) to palladium-catalyzed cross coupling reactions.Computed Properties of C7H5N3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A Specific Blend of Drakolide and Hydroxymethylpyrazines: An Unusual Pollinator Sexual Attractant Used by the Endangered Orchid Drakaea micrantha was written by Bohman, Bjoern;Tan, Monica M. Y.;Phillips, Ryan D.;Scaffidi, Adrian;Sobolev, Alexandre N.;Moggach, Stephen A.;Flematti, Gavin R.;Peakall, Rod. And the article was included in Angewandte Chemie, International Edition in 2020.COA of Formula: C8H12N2O This article mentions the following:

Bioactive natural products underpin the intriguing pollination strategy used by sexually deceptive orchids. These compounds, which mimic the sex pheromones of the female insect, are emitted in particular blends to lure male insect pollinators of specific species. By combining methods from field biol., anal. chem., electrophysiol., crystallog., and organic synthesis, we report that an undescribed β-hydroxylactone, in combination with two specific hydroxymethylpyrazines, act as pollinator attractants in the rare hammer orchid Drakaea micrantha. This discovery represents an unusual case of chem. unrelated compounds being used together as a sexual attractant. Furthermore, this is the first example of the identification of pollinator attractants in an endangered orchid, enabling the use of chem. in orchid conservation. Our synthetic blend is now available to be used in pollinator surveys to locate suitable sites for plant conservation translocations. 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 is an N-heterocyclic moiety, and it can be easily prepared from ethylenediamine and 1,2-diketone, α-hydroxyketone, α-methyl ketone. 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.COA of Formula: C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Structural determinants for AMPA agonist activity of aryl or heteroaryl substituted AMPA analogues. Synthesis and pharmacology was written by Sorensen, Ulrik S.;Falch, Erik;Stensbol, Tine B.;Jaroszewski, Jerzy W.;Madsen, Ulf;Krogsgaard-Larsen, Povl. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2001.Reference of 6924-68-1 This article mentions the following:

We have previously reported the synthesis and pharmacol. characterization of analogs of 2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) in which the Me group was replaced by a Ph group (APPA) or heteroaryl groups. While 2-amino-3-[3-hydroxy-5-(2-furyl)-4-isoxazolyl]propionic acid and its 3-pyridyl analog 2-amino-3-[3-hydroxy-5-(3-pyridyl)-4-isoxazolyl]propionic acid (3-Py-AMPA) show very low affinity for AMPA receptors, introduction of heteroaryl substituents containing heteroatom in the 2-position provides potent AMPA receptor agonists. We here report the synthesis and pharmacol. of 2-amino-3-(3-hydroxy-5-pyrazinyl-4-isoxazolyl)propionic acid (IC₅₀ = 1.2 μM; EC₅₀ = 11 μM), which is weaker as an AMPA agonist than AMPA (IC₅₀ = 0.040 μM; EC₅₀ = 3.5 μM) but comparable in potency with 2-amino-3-[3-hydroxy-5-(2-pyridyl)-4-isoxazolyl]propionic acid (IC₅₀ = 0.57 μM; EC₅₀ = 7.4 μM), as determined in radioligand binding and electrophysiol. experiments, resp. The AMPA analogs containing 2-, 3-, or 4-methoxyphenyl substituents, resp., and the corresponding hydroxyphenyl analogs were also synthesized and evaluated pharmacol. With the exception of 2-amino-3-[3-hydroxy-5-(2-hydroxyphenyl)-4-isoxazolyl]propionic acid, which is a very weak AMPA agonist (IC₅₀ = 45 μM; EC₅₀ = 324 μM), none of these compounds showed detectable effect at AMPA receptors. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Reference of 6924-68-1).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) 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.Reference of 6924-68-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Research of metabolic kinetics and reaction phenotyping of ligustrazin by using liver microsomes and recombinant human enzymes was written by Tan, Yan;Zhuang, Xiao-mei;Shen, Guo-lin;Li, Hua;Gao, Yue. And the article was included in Yaoxue Xuebao in 2014.Synthetic Route of C8H12N2O This article mentions the following:

The metabolic characteristics of ligustrazin (TMPz) in liver microsomes were studied. The reaction phenotyping of TMPz metabolism was also identified by in vitro assessment using recombinant human cytochrome P 450 enzymes (CYP) and UDP glucuronosyltransferases (UGT). TMPz was incubated at 37°C with human (HLM) and rat liver microsomes (RLM) in the presence of different co-factors. The metabolic stability and enzyme kinetics of TMPz were studied by determining its remaining concentrations with a LC-MS/MS method. TMPz was only metabolically eliminated in the microsomes with NADPH or NADPH+UDPGA. In the HLM and RLM with NADPH+UDPGA, t_1/2, K_m, and V_max of TMPz were 94.24±4.53 and 105.07±9.44 min, 22.74±1.89 and 33.09±2.74μmol·L^-1, 253.50±10.06 and 190.40±8.35 nmol·min^-1·mg^-1 (protein), resp. TMPz showed a slightly higher metabolic rate in HLM than that in RLM. Its primary oxidative metabolites, 2-hydroxymethyl-3,5,6-trimethylpyrazine (HTMP), could undergo glucuronide conjugation. The CYP reaction phenotyping of TMPz metabolism was identified using a panel of recombinant CYP isoforms (rCYP) and specific CYP inhibitors in HLM. CYP1A2, 2C9, and 3A4 were the major CYP isoforms involved in TMPz metabolism Their individual contributions were assessed by using the method of the total normalized rate to be 19.32, 27.79, and 52.90%, resp. It was observed that these CYP isoforms mediated the formation of HTMP in rCYP incubation. The UGT reaction phenotyping of HTMP glucuronidation was also studied preliminarily by using a panel of 6 UGT isoforms (rUGT). UGT1A1, 1A4, and 1A6 were the predominant isoforms mediated the HTMP glucuronidation. The results above indicated that the metabolism of TMPz involves multiple enzymes mediated phase I and phase II reactions. 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. 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.Synthetic Route of C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis of tetramethylpyrazine derivatives by Mitsunobu reaction was written by Wang, Hui-ying;Sun, Ping-hua;Chen, Wei-min. And the article was included in Hecheng Huaxue in 2011.Application of 75907-74-3 This article mentions the following:

Three tetramethylpyrazine derivatives I(R = H, MeO), and II in yields of 87%∼92% were synthesized by Mitsunobu reaction from tetramethylpyrazine. The structures were characterized by ¹H NMR, ¹³C NMR and ESI-MS. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Application of 75907-74-3).

(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 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.Application of 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem