M.W=200-250 Archives

Guo, Qi’s team published research in Chemical Papers in 73 | CAS: 1257072-34-6

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.

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.

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

Karroum, Nour Bou’s team published research in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 54 | CAS: 117718-92-0

Chemistry of Heterocyclic Compounds (New York, NY, United States) published new progress about 117718-92-0. 117718-92-0 belongs to pyrazines, auxiliary class Other Aromatic Heterocyclic,Bromide,Amine, name is 3-Bromoimidazo[1,2-a]pyrazin-8-amine, and the molecular formula is C6H5BrN4, Formula: C6H5BrN4.

Karroum, Nour Bou published the artcileMethylation of imidazopyrazine, imidazoquinoxaline, and pyrazoloquinoxaline through Suzuki-Miyaura cross coupling, Formula: C6H5BrN4, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2018), 54(2), 183-187, database is CAplus.

The methylation of bromo derivatives of imidazopyrazine, imidazoquinoxaline, and pyrazoloquinoxaline e.g., 3-bromo-N-methylimidazo[1,2-a]pyrazin-8-amine having biol. interesting structures were described. As the challenging Suzuki-Miyaura reaction is highly substrate dependent, the choices of the base, solvent, and additive are also discussed.

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

Bonnet, Pierre A.’s team published research in Journal of Medicinal Chemistry in 35 | CAS: 117718-92-0

Journal of Medicinal Chemistry published new progress about 117718-92-0. 117718-92-0 belongs to pyrazines, auxiliary class Other Aromatic Heterocyclic,Bromide,Amine, name is 3-Bromoimidazo[1,2-a]pyrazin-8-amine, and the molecular formula is C6H5BrN4, HPLC of Formula: 117718-92-0.

Bonnet, Pierre A. published the artcileSynthesis and antibronchospastic activity of 8-alkoxy- and 8-(alkylamino)imidazo[1,2-a]pyrazines, HPLC of Formula: 117718-92-0, the publication is Journal of Medicinal Chemistry (1992), 35(18), 3353-8, database is CAplus and MEDLINE.

Theophylline still occupies a dominant place in asthma therapy. Unfortunately its adverse central nervous system stimulant effects can dramatically limit its use, and adjustments in the dosage are often needed. We have synthesized a new series of imidazo[1,2-a]pyrazine derivatives which are much more potent bronchodilators than theophylline in vivo and do not exhibit the CNS stimulatory profile. In vitro studies on isolated rat uterus and guinea pig trachea confirm the high potentialities of these derivatives 6-Bromo-8-(methylamino)imidazo[1,2-a]pyrazine-3-carbonitrile is identified as the most potent compound of the series. As in the case of theophylline, phosphodiesterase inhibition appears unlikely to be the unique mechanism of action of this series of heterocycles.

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

Gao, Ling-Jie’s team published research in Journal of Medicinal Chemistry in 57 | CAS: 1257072-34-6

Journal of Medicinal Chemistry 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, SDS of cas: 1257072-34-6.

Gao, Ling-Jie published the artcileDiscovery of Dual Death-Associated Protein Related Apoptosis Inducing Protein Kinase 1 and 2 Inhibitors by a Scaffold Hopping Approach, SDS of cas: 1257072-34-6, the publication is Journal of Medicinal Chemistry (2014), 57(18), 7624-7643, database is CAplus and MEDLINE.

DRAK2 emerged as a promising drug target for the treatment of autoimmune diseases and to prevent graft rejection after organ transplantation. Screening of a compound library in a DRAK2 binding assay led to the identification of an isothiazolo[5,4-b]pyridine derivative as a novel ligand for DRAK2, displaying a K_d value of 1.6 μM. Subsequent medicinal chem. work led to the discovery of a thieno[2,3-b]pyridine derivative with strong DRAK2 binding affinity (K_d = 9 nM). Moreover, this compound also behaves as a functional inhibitor of DRAK2 enzymic activity, displaying an IC₅₀ value of 0.82 μM, although lacking selectivity, when tested against DRAK1. This paper describes for the first time functionally active dual DRAK1 and DRAK2 inhibitors that can be used as starting point for the synthesis of chem. tool compounds to study DRAK1 and DRAK2 biol., or they can be considered as hit compounds for hit-to-lead optimization campaigns in drug discovery programs.

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

Garamvolgyi, Rita’s team published research in European Journal of Medicinal Chemistry in 108 | CAS: 117718-92-0

European Journal of Medicinal Chemistry published new progress about 117718-92-0. 117718-92-0 belongs to pyrazines, auxiliary class Other Aromatic Heterocyclic,Bromide,Amine, name is 3-Bromoimidazo[1,2-a]pyrazin-8-amine, and the molecular formula is C6H5BrN4, Application In Synthesis of 117718-92-0.

Garamvolgyi, Rita published the artcileDesign and synthesis of new imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrazine derivatives with antiproliferative activity against melanoma cells, Application In Synthesis of 117718-92-0, the publication is European Journal of Medicinal Chemistry (2016), 623-643, database is CAplus and MEDLINE.

A new series of diarylamide and diarylurea derivatives containing imidazo[1,2-a]pyridine or imidazo[1,2-a]pyrazine scaffold I (R = H, 3,5-F, 3-CF₃, etc.), II, III was designed and synthesized to investigate their in vitro efficacy against the A375P human melanoma cell line. Several compounds expressing submicromolar IC₅₀ values against the A375P cells was observed, from which I (R = 3,5-F), II (R = 3,5-Cl), III (R = 3,5-Cl, 3,5-(CF₃)₂, 4-F-3-CF₃) demonstrated the highest potencies with IC₅₀ below 0.06 μM.

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

Patinote, Cindy’s team published research in European Journal of Medicinal Chemistry in 212 | CAS: 117718-92-0

Patinote, Cindy published the artcileImidazo[1,2-a]quinoxalines for melanoma treatment with original mechanism of action, Formula: C6H5BrN4, the publication is European Journal of Medicinal Chemistry (2021), 113031, database is CAplus and MEDLINE.

The malignant transformation of melanocytes causes several thousand deaths each year, making melanoma an important public health concern. Melanoma is the most aggressive skin cancer, which incidence has regularly increased over the past decades. We described here the preparation of new compounds based on the 1-(3,4-dihydroxyphenyl)imidazo[1,2-a]quinoxaline structure. Different positions of the quinoxaline moiety were screened to introduce novel substituents in order to study their influence on the biol. activity. Several alkylamino or alkyloxy groups were also considered to replace the methylamine of our first generation of Imiqualines. Imidazo[1,2-a]pyrazine derivatives were also designed as potential minimal structure. The investigation on A375 melanoma cells displayed interesting in vitro low nanomolar cytotoxic activity. Among them, 9d (EAPB02303) is particularly remarkable since it is 20 times more potent than vemurafenib, the reference clin. therapy used on BRAF mutant melanoma. Contrary to the first generation, EAPB02303 does not inhibit tubulin polymerization, as confirmed by an in vitro assay and a mol. modelisation study. The mechanism of action for EAPB02303 highlighted by a transcriptomic anal. is clearly different from a panel of 12 well-known anticancer drugs. In vivo EAPB02303 treatment reduced tumor size and weight of the A375 human melanoma xenografts in a dose-dependent manner, correlated with a low mitotic index but not with necrosis.

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

Patinote, Cindy’s team published research in European Journal of Medicinal Chemistry in 138 | CAS: 117718-92-0

Patinote, Cindy published the artcileImidazo[1,2-a]pyrazine, Imidazo[1,5-a]quinoxaline and Pyrazolo[1,5-a]quinoxaline derivatives as IKK1 and IKK2 inhibitors, Related Products of pyrazines, the publication is European Journal of Medicinal Chemistry (2017), 909-919, database is CAplus and MEDLINE.

Herein, the synthesis of twenty-one new compounds based on the imidazo[1,2-a]pyrazine, imidazo[1,5-a]quinoxaline or pyrazolo[1,5-a]quinoxaline structures is reported. Their potential to inhibit IKK1 and IKK2 activities is also tested.

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

Meti, Puttavva’s team published research in RSC Advances in 2017 | CAS: 960510-36-5

RSC Advances published new progress about Amination. 960510-36-5 belongs to class pyrazines, name is 5-Bromo-3,6-dichloropyrazin-2-amine, and the molecular formula is C4H2BrCl2N3, Safety of 5-Bromo-3,6-dichloropyrazin-2-amine.

Meti, Puttavva published the artcileRegioselective synthesis of dipyrrolopyrazine (DPP) derivatives via metal free and metal catalyzed amination and investigation of their optical and thermal properties, Safety of 5-Bromo-3,6-dichloropyrazin-2-amine, the main research area is dipyrrolopyrazine derivative preparation regioselective; dihalo pyrrolopyrazine alkyne metal catalyst amination reaction.

An efficient methods for the synthesis of dipyrrolopyrazine derivatives, I [R1 = H, C6H5; R2 = C6H5, 4-F-C6H4, (CH3)2NC6H4, cyclopropyl, etc.] and II and pyrrolothieno-pyrazine derivatives, III (X = H, C6H5) that involve regioselective amination reactions of dihalo-pyrrolopyrazines IV [Y = H, CH3, 4-CH3C6H4S(O)2; A = Br; B = Cl] is reported. The developed protocol readily affords either 2-amino- or 3-amino-pyrrolopyrazines IV (A = Br, NHCH3; B = Cl, NHCH3) from the corresponding 2-bromo-3-chloro-5H-pyrrolo[2,3-b]pyrazines IV (A = Br; B = Cl). When the amination reactions was carried under metal-free microwave irradiation, 3-amino-pyrrolopyrazines IV (A = Br; B = NHCH3) was obtained exclusively. In contrast, Buchwald cross coupling of the 2-bromo-3-chloro-5H-pyrrolo[2,3-b]pyrazines IV (A = Br; B = Cl) affords only 2-amino-pyrrolopyrazine IV (A = NHCH3; B = Cl). The pyrrolopyrazine scaffolds was converted to the resp. 1,7- I and 1,5-dihydrodipyrrolo[2,3-b]pyrazines derivatives II using Sonogashira reactions. A comprehensive study of the optical properties, thermal properties, and mol. packing of the synthesized compounds was carried out. The results indicate that the 1,7-derivatives I may be promising organic materials for optoelectronic applications.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Zhang, Hua’s team published research in Natural Product Research in 2020 | 2873-36-1

Natural Product Research published new progress about Diketopiperazines Role: BSU (Biological Study, Unclassified), NPO (Natural Product Occurrence), PAC (Pharmacological Activity), PRP (Properties), PUR (Purification or Recovery), BIOL (Biological Study), OCCU (Occurrence), PREP (Preparation). 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Safety of (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione.

Zhang, Hua; Lai, Wei; Guan, Zhuo-Bin; Liao, Xiao-Jian; Zhao, Bing-Xin; Xu, Shi-Hai published the artcile< A new thiodiketopiperzaine from the marine sponge Tedania sp.>, Safety of (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione, the main research area is diketopiperzaine isolation structure sponge; Sponge; Tedania sp.; thiodiketopiperzaine.

A new thiodiketopiperzaine, tedanizaine A (I), together with 6 known ones, were isolated from the marine sponge Tedania sp. Their structures were determined by spectroscopic analyses. The absolute configuration of I was established by ECD calculation I was the 2nd example of thiodiketopiperazine bearing a thiazolidine unit. Cytotoxic activities of I were also evaluated.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Bai, Meng’s team published research in Chemistry of Natural Compounds in 2022-03-31 | 2873-36-1

Chemistry of Natural Compounds published new progress about Antibacterial agents. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Quality Control of 2873-36-1.

Bai, Meng; He, Jia-Li; Gao, Cheng-Hai; Xiong, Fei-Xiang; Yang, Ya; Yang, Wei-Chan; Liu, Yong-Hong; Zhang, Wen-Fei published the artcile< Secondary Metabolites from Bacillus thuringiensis HS66>, Quality Control of 2873-36-1, the main research area is Bacillus Helicoverpa larva secondary metabolite.

In order to search for the bioactive chem. constituents from the B. thuringiensis, 12 compounds were isolated from the EtOAc extract of the B. thuringiensis. The isolated compoundswere identified as cyclo(L-Pro-L-Tyr) (1) [6], cyclo(Pro-Phe) (2) [7], cyclo(L-Pro-L-Phe) (3) [8], cyclo(Pro-Val) (4) [9], cyclo(L-Pro-L-Met) (5) [10], cyclo((S)-Pro-(R)-Ile) (6) [11], cyclo(L-Pro-L-Leu) (7) [12], N-(2-hydroxyphenyl)acetamide (8) [13], uracil (9) [13], 2-phenylacetamide (10) [14], anthranilic acid (11) [15], and S-(4-hydroxyphenyl)lactic acid (12) [16]. The growth inhibition activity against newly hatched larvae of Helicoverpa armigera Hubner was tested. Compounds 1-3, 6, 7, and 10 showed growth inhibition activity against newly hatched larvae of Helicoverpa armigera Hubner with IC 50 values ranging from 50 to 200 μg/mL. Azadirachtin was used as pos. control with the IC50 value of 25 μg/mL.

Chemistry of Natural Compounds published new progress about Antibacterial agents. 2873-36-1 belongs to class pyrazines, and the molecular formula is C11H18N2O2, Quality Control of 2873-36-1.

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem