117718-92-0

Basic information

• Product Name: 3-BROMOIMIDAZO[1,2-A]PYRAZIN-8-AMINE
• Synonyms: 3-BROMOIMIDAZO[1,2-A]PYRAZIN-8-AMINE;8-AMino-3-broMoiMidazo[1,2-a]pyrazine
• CAS NO: 117718-92-0
• Molecular Formula: C₆H₅BrN₄
• Molecular Weight: 213.04
• Mol File: 117718-92-0.mol

Chemical Properties

• Appearance: /
• Density: 2.098 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 3-BROMOIMIDAZO[1,2-A]PYRAZIN-8-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMOIMIDAZO[1,2-A]PYRAZIN-8-AMINE(117718-92-0)
• EPA Substance Registry System: 3-BROMOIMIDAZO[1,2-A]PYRAZIN-8-AMINE(117718-92-0)

Safety Data

• Hazardous Substances Data: 117718-92-0(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
3-Bromoimidazo[1,2-a]pyrazin-8-amine is used as a compound with potential biological activities for the development of new drugs and therapeutic agents. Its unique structure and functional groups may allow for interactions with biological targets, making it a candidate for further exploration in drug discovery.
Used in Drug Design:
3-Bromoimidazo[1,2-a]pyrazin-8-amine is used as a building block in the design of novel pharmaceutical compounds. Its presence of a bromine atom and amine group can be exploited to create derivatives with specific properties, potentially leading to the development of new drugs with improved efficacy and selectivity.
Used in Research Applications:
3-Bromoimidazo[1,2-a]pyrazin-8-amine is used as a research tool in the study of imidazo[1,2-a]pyrazine chemistry and its potential applications. It can serve as a starting material for the synthesis of more complex molecules or as a probe to investigate the biological activity of related compounds.

Upstream product

• 69214-33-1 8-chloroimidazo[1,2-α]pyrazine 
• 143591-61-1 3-bromo-8-chloro-imidazo[1,2-a]pyrazine 
• 63744-21-8 3,5-dibromoimidazo<1,2-a>pyrazine 
• 936361-36-3 3,8-dibromo-imidazo[1,2-a]pyrazine 
• 274-79-3 imidazo[1,2-a]pyrazine 

Downstream Products

• 787590-48-1 3-(4-amino-phenyl)-imidazo[1,2-a]pyrazin-8-ylamine 

Relevant articles and documents

Imidazo[1,2-a]quinoxalines for melanoma treatment with original mechanism of action

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 biological 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 clinical 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 molecular modelisation study. The mechanism of action for EAPB02303 highlighted by a transcriptomic analysis 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.

Design and synthesis of new imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrazine derivatives with antiproliferative activity against melanoma cells

Melanoma is an aggressive form of skin cancer and it is generally associated with poor prognosis in patients with late-stage disease. Due to the increasing occurrence of melanoma, there is a need for the development of novel therapies. A new series of diarylamide and diarylurea derivatives containing imidazo[1,2-a]pyridine or imidazo[1,2-a]pyrazine scaffold was designed and synthesized to investigate their in vitro efficacy against the A375P human melanoma cell line. We found several compounds expressing submicromolar IC50 values against the A375P cells, from which 15d, 17e, 18c, 18h, 18i demonstrated the highest potencies with IC50 below 0.06 μM.

Imidazo[1,2-a]pyrazine, Imidazo[1,5-a]quinoxaline and?Pyrazolo[1,5-a]quinoxaline derivatives as IKK1 and IKK2 inhibitors

The transcription nuclear factor NF-κB plays a pivotal role in chronic and acute inflammatory diseases. Among the several and diverse strategies for inhibiting NF-κB, one of the most effective approach considered by the pharmaceutical industry seems to be

IRE1α MODULATORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the modulation of IRE1α, and the treatment of IRE1α-mediated disorders.

Methods for inhibiting protein kinases

The present invention provides methods for inhibiting protein kinases selected from the group consisting of AKT, Checkpoint kinase, Aurora kinase, Pim-1 kinase, and tyrosine kinase using imidazo[1,2-a]pyrazine compounds and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with protein kinases using such compounds.

Imidazopyrazines as protein kinase inhibitors

In its many embodiments, the present invention provides a novel class of imidazopyrazine compounds as inhibitors of protein and/or checkpoint kinases, methods of preparing such compounds, pharmaceutical compositions including one or more such compounds, methods of preparing pharmaceutical formulations including one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the protein or checkpoint kinases using such compounds or pharmaceutical compositions.

Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors

The present invention relates to 8-amino-aryl-substituted imidazopyrazines which modulate the activity of protein kinases (“PKs”). The compounds of this invention are therefore useful in treating disorders related to abnormal PK activity. Pharmaceutical compositions comprising these compounds, methods of treating diseases utilizing pharmaceutical compositions comprising these compounds and methods of preparing them are also disclosed.

Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhbitors

The present invention relates to 8-amino-aryl-substituted imidazopyrazines which modulate the activity of protein kinases (“PKs”). The compounds of this invention are therefore useful in treating disorders related to abnormal PK activity. Pharmaceutical compositions comprising these compounds, methods of treating diseases utilizing pharmaceutical compositions comprising these compounds and methods of preparing them are also disclosed.

Synthesis and Antibronchospastic Activity of 8-Alkoxy- and 8-(Alkylamino)imidazopyrazines

Theophylline still occupies a dominant place in asthma therapy.Unfortunatly its adverse central nervous system (CNS) stimulant effects can dramatically limit its use, and adjustments in the dosage are often needed.We have synthesized a new series of imidazopyrazine 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)imidazopyrazine-3-carbonitrile (23) is identified as the most potent compound of the series.As i n the case of theophylline, phosphodiesterase inhibition appears unlikely to be the unique mechanism of the action of this series of heterocycles.

8-alkylaminoimidazo(1,2-a)pyrazines and derivatives, their preparation and their application in therapy

STR1 Novel 8-alkylamino-imidazo(1,2-a)pyrazines of formula (I) show advantages pharmacological activities. They can be used for medical products in human and veterinary therapy in the field of applications of antispasmodics, uterine relaxants, bronchodila