Month: November 2022

Zhai, Xin published the artcileSynthesis and antibacterial activities of 3-fluoro-4-(2-arylthiazol-4-yl)phenyloxazolidinone derivatives, Recommanded Product: Pyrazine-2-carbothioamide, the publication is Shenyang Yaoke Daxue Xuebao (2007), 24(5), 275-279, database is CAplus.

Fourteen new 3-fluoro-4-(2-arylthiazol-4-yl)phenyloxazolidinone derivatives was prepared from 2-chloromethyloxrane and 3-fluorophenyl isocyanate in seven steps to provide the target products and their structures are confirmed by ¹H NMR and MS. Primary in vitro antibacterial activity test indicated that ten of them show antibacterial activities.

Shenyang Yaoke Daxue Xuebao published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C3H12Cl2N2, Recommanded Product: Pyrazine-2-carbothioamide.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Guo, Qi published the artcileThe complete synthesis of favipiravir from 2-aminopyrazine, Category: pyrazines, the publication is Chemical Papers (2019), 73(5), 1043-1051, database is CAplus.

Favipiravir was synthesized from an inexpensive and com. available starting material, 2-aminopyrazine. The preferred route embedded within seven steps and was highlighted by the novel and efficient synthesis of 3,6-dichloropyrazine-2-carbonitrile. The intermediate 3,6-dichloropyrazine-2-carbonitrile was prepared in four successive steps which were regioselective chlorination of the pyrazine ring, bromination, Pd-catalyzed cyanation and Sandmeyer diazotization/chlorination. This protocol eliminated the hazardous POCl₃ of previous synthetic methods and offered a better yield (48%) which was 1.3-fold higher than a recently published procedure. From intermediate 3,6-dichloropyrazine-2-carbonitrile, the subsequent nucleophilic fluorination, nitrile hydration and hydroxyl substitution efficiently afforded the target product. Another synthetic approach with the same starting material was also investigated to bypass the allergy-causing dichloro intermediate 3,6-dichloropyrazine-2-carbonitrile. The key step of monofluorination at the pyrazine C6 position of intermediate 6-chloro/bromo-3-aminopyrazine-2-carbonitriles and 6-chloro/bromo-3-hydroxylpyrazine-2-carbonitriles was not achieved.

Chemical Papers published new progress about 1257072-34-6. 1257072-34-6 belongs to pyrazines, auxiliary class Pyrazine,Chloride,Nitrile,Bromide, name is 6-Bromo-3-chloropyrazine-2-carbonitrile, and the molecular formula is C5HBrClN3, Category: pyrazines.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Guernon, Jason M. published the artcile3-Bromocyclohexane-1,2-dione as a useful reagent for Hantzsch synthesis of thiazoles and the synthesis of related heterocycles, Safety of Pyrazine-2-carbothioamide, the publication is Tetrahedron Letters (2011), 52(28), 3633-3635, database is CAplus.

The authors describe the use of 3-bromocyclohexane-1,2-dione, an air stable, versatile reagent for the Hantzsch thiazole synthesis and the synthesis of other closely related heterocycles. For example, cyclocondensation of 3-bromocyclohexane-1,2-dione with RC(S)NH₂ (R = Ph, 4-pyridyl, t-Bu, etc.) gave I.

Tetrahedron Letters published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C5H5N3S, Safety of Pyrazine-2-carbothioamide.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Melancon, Bruce J. published the artcileOptimization of M₄ pos. allosteric modulators (PAMs): The discovery of VU0476406, a non-human primate in vivo tool compound for translational pharmacol., Related Products of pyrazines, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(11), 2296-2301, database is CAplus and MEDLINE.

Optimization of M₄ pos. allosteric modulators (PAMs): The discovery of VU0476406, a non-human primate in vivo tool compound for translational pharmacol. This letter describes the further chem. optimization of the 5-amino-thieno[2,3-c]pyridazine series (VU0467154/VU0467485) of M₄ pos. allosteric modulators (PAMs), developed via iterative parallel synthesis, culminating in the discovery of the non-human primate (NHP) in vivo tool compound, VU0476406 (8p). VU0476406 is an important in vivo tool compound to enable translation of pharmacodynamics from rodent to NHP, and while data related to a Parkinson’s disease model has been reported with 8p, this is the first disclosure of the optimization and discovery of VU0476406, as well as detailed pharmacol. and DMPK properties.

Bioorganic & Medicinal Chemistry Letters published new progress about 762263-64-9. 762263-64-9 belongs to pyrazines, auxiliary class Pyrazine,Boronic acid and ester,Boronic Acids, name is Pyrazin-2-ylboronic acid, and the molecular formula is C4H5BN2O2, Related Products of pyrazines.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

East, Stephen P. published the artcileDNA gyrase (GyrB)/topoisomerase IV (ParE) inhibitors: Synthesis and antibacterial activity, Category: pyrazines, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(3), 894-899, database is CAplus and MEDLINE.

The synthesis and antibacterial activities of three chemotypes of DNA supercoiling inhibitors based on imidazo[1,2-a]pyridine and [1,2,4]triazolo[1,5-a]pyridine scaffolds, e.g. I (R = H, Ph, 2-HOC₆H₄, 2-pyridyl, 5-pyrimidyl, 1-imidazolyl, CO₂Me, CONHEt, etc.), that target the ATPase subunits of DNA gyrase and topoisomerase IV (GyrB/ParE) is reported. The most potent scaffold was selected for optimization leading to a series with potent Gram-pos. antibacterial activity and a low resistance frequency.

Bioorganic & Medicinal Chemistry Letters published new progress about 762263-64-9. 762263-64-9 belongs to pyrazines, auxiliary class Pyrazine,Boronic acid and ester,Boronic Acids, name is Pyrazin-2-ylboronic acid, and the molecular formula is C4H5BN2O2, Category: pyrazines.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Liu, Zong-ying published the artcileSynthesis and antiparasitic activity of new bis-arylimidamides: DB766 analogs modified in the terminal groups, Computed Properties of 4604-72-2, the publication is European Journal of Medicinal Chemistry (2014), 167-173, database is CAplus and MEDLINE.

Fifteen novel bis-arylimidamide derivatives with various 6-membered and 5-membered heterocyclic rings replacing the terminal pyridyl rings of the lead compound DB766, were prepared and evaluated vs. Trypanosoma cruzi, Leishmania amazonensis, Trypanosoma brucei rhodesiense and Plasmodium falciparum. Compound I(R = 2-pyrimidyl) with pyrimidine replacing the pyridine rings showed good activity vs. T. cruzi, T. brucei rhodesiense and P. falciparum (IC₅₀ = 200 nM, 32 nM and 8.5 nM, resp.). Three compounds I(R = 2-methyl-4-thiozolyl, 2-methylamino-4-thiozolyl, 2-acetylamino-4-thiozolyl) with thiazole replacing the pyridine rings gave low micromolar (0.17-0.3 μM) IC₅₀ values vs. L. amazonensis, however only 7g exhibited an acceptable selectivity index (SI = 27). Compounds I(R = 2-pyrimidyl, 2-acetylamino-4-thiozolyl, 2-imidazolyl) exhibited potent activity against T. brucei rhodesiense (IC₅₀ = 12-60 nM). Ten of the 15 compounds with pyrimidine, pyrrole, thiazole and imidazole terminal units were highly active against P. falciparum (IC₅₀ = 9-87 nM). Both pyrimidine and pyridine terminal groups are advantageous for anti-T. cruzi activity and several different heterocyclic terminal units are effective vs. P. falciparum, both findings merit further investigation.

European Journal of Medicinal Chemistry published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C5H5N3S, Computed Properties of 4604-72-2.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Taeuscher, Eric published the artcileSynthesis and characterization of new 4-hydroxy-1,3-thiazoles, Computed Properties of 4604-72-2, the publication is Synthesis (2010), 1603-1608, database is CAplus.

A series of highly substituted 4-hydroxy-1,3-thiazoles was synthesized by cyclocondensation of α-bromo carboxylates with thioamides or of thiolactate with 2-quinoxalinecarbonitrile. Whereas their anions display strong fluorescence in the bathochromic part of the visible spectrum, the emission is shifted hypsochromically upon alkylation. This easy switch between the anion and its derivatives makes them suitable for widespread applications. The thiazoles possess prerequisites for the complexation of metals due to the coexistence of aza-heterocycles and of 1,3-diketone substructures. In addition, the OH group allows further functionalization, as exemplified by the incorporation of an azide or an acetylene into the product, and by the synthesis of a star-shaped derivative The mol. and crystal structure of 2-(1,5-dimethylpyrrol-2-yl)-5-phenyl-4-thiazolol was presented [monoclinic, space group P2₁/n, a 6.7533(2), b 20.6146(6), c 9.9435(3) Å, β 109.062(2)°, V 1308.39(7) ų, Z 4].

Synthesis published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C3H9ClOS, Computed Properties of 4604-72-2.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Johns, Brian A. published the artcile1,3,4-Oxadiazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 2: SAR of the C5 position, Safety of Pyrazin-2-ylboronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(6), 1807-1810, database is CAplus and MEDLINE.

The use of a 1,3,4-oxadiazole in combination with an 8-hydroxy-1,6-naphthyridine ring system has been shown to deliver potent enzyme and antiviral activity through inhibition of viral DNA integration. This report presents a detailed structure-activity investigation of the C5 position resulting in low nM potency for several analogs with an excellent therapeutic index.

Bioorganic & Medicinal Chemistry Letters published new progress about 762263-64-9. 762263-64-9 belongs to pyrazines, auxiliary class Pyrazine,Boronic acid and ester,Boronic Acids, name is Pyrazin-2-ylboronic acid, and the molecular formula is C4H5BN2O2, Safety of Pyrazin-2-ylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Kayser, A. published the artcileGrowth inhibition of staphylococci by sodium thiosulfate, Product Details of C5H5N3S, the publication is Journal of Applied Bacteriology (1965), 28(2), 286-93, database is CAplus and MEDLINE.

Several strains of staphylococci and micrococci used as test organisms for I disinfectant assay were inhibited by the Na thiosulfate used to neutralize residual I. The action was not due to changes in pH or redox potential, but was most pronounced in media containing high concentrations of cystine.

Journal of Applied Bacteriology published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C5H5N3S, Product Details of C5H5N3S.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Wang, Tao published the artcileDiscovery of the Human Immunodeficiency Virus Type 1 (HIV-1) Attachment Inhibitor Temsavir and Its Phosphonooxymethyl Prodrug Fostemsavir, Safety of Pyrazin-2-ylboronic acid, the publication is Journal of Medicinal Chemistry (2018), 61(14), 6308-6327, database is CAplus and MEDLINE.

The optimization of the 4-methoxy-6-azaindole series of HIV-1 attachment inhibitors (AIs) that originated with 1 to deliver temsavir (3, BMS-626529) is described. The most beneficial increases in potency and pharmacokinetic (PK) properties were attained by incorporating N-linked, sp²-hybridized heteroaryl rings at the 7-position of the heterocyclic nucleus. Compounds that adhered to a coplanarity model afforded targeted antiviral potency, leading to the identification of 3 with characteristics that provided for targeted exposure and PK properties in three preclin. species. However, the phys. properties of 3 limited plasma exposure at higher doses, both in preclin. studies and in clin. trials as the result of dissolution- and/or solubility-limited absorption, a deficiency addressed by the preparation of the phosphonooxymethyl prodrug 4 (BMS-663068, fostemsavir). An extended-release formulation of 4 is currently in phase III clin. trials where it has shown promise as part of a drug combination therapy in highly treatment-experienced HIV-1 infected patients.

Journal of Medicinal Chemistry published new progress about 762263-64-9. 762263-64-9 belongs to pyrazines, auxiliary class Pyrazine,Boronic acid and ester,Boronic Acids, name is Pyrazin-2-ylboronic acid, and the molecular formula is C7H10BNO4S, Safety of Pyrazin-2-ylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem