Category: 79707-11-2

Abe, Yoshito; Kayakiri, Hiroshi; Satoh, Shigeki; Inoue, Takayuki; Sawada, Yuki; Imai, Keisuke; Inamura, Noriaki; Asano, Masayuki; Hatori, Chie; Katayama, Akira; Oku, Teruo; Tanaka, Hirokazu published an article on February 12 ,1998. The article was titled 《A Novel Class of Orally Active Non-Peptide Bradykinin B2 Receptor Antagonists. 1. Construction of the Basic Framework》, and you may find the article in Journal of Medicinal Chemistry.Product Details of 79707-11-2 The information in the text is summarized as follows:

A novel class of potent, selective, and orally active non-peptide bradykinin (BK) B2 receptor antagonists were designed and synthesized starting from 8-benzyloxyimidazo[1,2-a]pyridine derivative(I). The unique screening lead I was discovered by a 2-step intentional random screening process, involving recognition of the relationship between BK and angiotensin II (Ang II) and the common structural features. Systematic chem. modification of I elucidated the structural requirements essential for B2 binding affinity leading to the identification of 8-[[3-(N-acylglycyl-N-methylamino)-2,6-dichlorobenzyl]oxy]-3-halo-2-methylimidazo[1,2-a]pyridine skeleton as the basic framework of this new series of B2 antagonists. A mol. modeling study suggested the key role of the N-methylanilide moiety at the 3-position of the 2,6-dichlorobenzene ring to allow these compounds to adopt the characteristic active conformation. The representative lead compounds inhibited the specific binding of [3H]BK to guinea pig ileum membrane preparations expressing B2 receptors, with nanomolar IC50s and also displayed in vivo functional antagonistic activities against BK-induced bronchoconstriction in guinea pigs at an oral dose of 1 mg/kg. Pharmacokinetic studies of the N-butylamide and Et urea moieties at the 3-position of the 2,6-dichlorobenzene in rats highlighted their excellent oral bioavailabilities, indicating that they represent the first orally active non-peptide B2 antagonists reported to date. In the experiment, the researchers used 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Product Details of 79707-11-2)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies. Product Details of 79707-11-2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Cationic heteroaromatic carbamates as acetylcholinesterase inhibitors. Synthesis and inhibitory activity of 5-, 6-, 7- and 8-carbamoyloxy derivatives of 2-substituted imidazo[1,2-a]pyridinium salts》 were Sundberg, Richard J.; Van Nguyen, Phuoc; Jiang, Songchun. And the article was published in Medicinal Chemistry Research in 1997. Formula: C8H8N2O The author mentioned the following in the article:

A series of 1-Me 5-, 6-, 7-, and 8-N,N-dimethylcarbamoyloxy derivatives of imidazo[1,2-a]pyridinium salts with varying 2-substituents (H, Me, Me2CH, Ph) was prepared The inhibitory activity against acetylcholinesterase (AChE) was determined The 5- and 8-substituted compounds are active as AChE inhibitors in the submicromolar range and show significant acute toxicity. The AChE inhibitory activity decreased in the order 5>8>7>6 as the position of substitution. Some of the compounds were also evaluated for protective effects against soman in mice. Several of the compounds have modest protective effects against 2LD50 soman. In the part of experimental materials, we found many familiar compounds, such as 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Formula: C8H8N2O)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies. Formula: C8H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Antiulcer agents. 1. Gastric antisecretory and cytoprotective properties of substituted imidazo[1,2-a]pyridines》 were Kaminski, James J.; Bristol, James A.; Puchalski, Chester; Lovey, Raymond G.; Elliott, Arthur J.; Guzik, Henry; Solomon, Daniel M.; Conn, David J.; Domalski, Martin S.. And the article was published in Journal of Medicinal Chemistry in 1985. Computed Properties of C8H8N2O The author mentioned the following in the article:

The title compounds (I; R = H, OH, CHO, PhO, (un)substituted benzyloxy, PhCH2NH, etc.; R1 = H, or PhCH2CH2; R2 = H, Me, Et, CHMe2; R3 = H, Me, CO2H, CO2Et, CN, CH2CN, etc.), prepared in general by condensation of substituted 2-aminopyridines with α-halocarbonyls, were evaluated for gastric antisecretory activity in the pylorus-ligated rat and inhibition of histamine-stimulated gastric secretion in the adult dog and gastric cytoprotective activity in the rat. In the pylorus-ligated rat, I were given at 40 mg/kg i.p., at time of ligation and reduction in acid output was measured after 4 h, and in the dog I was 1st administered i.v. 0.1-5 mg/kg and reduction in the acid output relative to nondrug-treated control value in the same animal was measured. For gastric cytoprotective activity I was given orally 1-30 mg/kg 30 min before oral administration of absolute EtOH, and the effect against EtOH-induced lesions was determined after 1 h. The results show that I are not histamine (H2) receptor antagonists nor are they prostaglandin analogs, yet they exhibit both gastric antisecretory and cytoprotective properties. The mechanism of gastric antisecretory activity may involve inhibition of H+/K+-ATPase. 3-(Cyanomethyl)-2-methyl-8-(phenylmethoxy)imidazo[1,2-a]pyridine (I); R = PhCH2O, R1 = H, R2 = Me, R3 = CH2CN)(SCH 28080) [76081-98-6] was selected for clin. evaluation. Structure-activity relations are discussed. The results came from multiple reactions, including the reaction of 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Computed Properties of C8H8N2O)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. Computed Properties of C8H8N2O In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of C8H8N2OOn June 1, 2020, Sekioka, Ryuichi; Honda, Shugo; Akashiba, Hiroki; Yarimizu, Junko; Mitani, Yasuyuki; Yamasaki, Shingo published an article in Bioorganic & Medicinal Chemistry. The article was 《Optimization and biological evaluation of imidazopyridine derivatives as a novel scaffold for γ-secretase modulators with oral efficacy against cognitive deficits in Alzheimer′s disease model mice》. The article mentions the following:

Gamma-secretase modulators (GSMs) selectively lower amyloid-β42 (Aβ42) and are therefore potential disease-modifying drugs for Alzheimer′s disease (AD). Here, we report the discovery of imidazopyridine derivatives as GSMs with oral activity on not only Aβ42 levels but also cognitive function. Structural optimization of the biphenyl group and pyridine-2-amide moiety of compound 1a greatly improved GSM activity and rat microsomal stability, resp. 5-{8-[(3,4′-Difluoro[1,1′-biphenyl]-4-yl)methoxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-N-methylpyridine-2-carboxamide (1o)(I) showed high in vitro potency and brain exposure, induced a robust reduction in brain Aβ42 levels, and exhibited undetectable inhibition of cytochrome P 450 enzymes. Moreover, compound 1o showed excellent efficacy against cognitive deficits in AD model mice. These findings suggest that compound 1o is a promising candidate for AD therapeutics. The results came from multiple reactions, including the reaction of 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Electric Literature of C8H8N2O)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
Electric Literature of C8H8N2O However, the application of imidazoles is not limited to the field of peptides and peptidomimetics.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Antiulcer agents. 2. Gastric antisecretory, cytoprotective, and metabolic properties of substituted imidazo[1,2-a]pyridines and analogs》 was published in Journal of Medicinal Chemistry in 1987. These research results belong to Kaminski, James J.; Hilbert, James M.; Pramanik, B. N.; Solomon, Daniel M.; Conn, David J.; Rizvi, Razia K.; Elliott, Arthur J.; Guzik, Henry; Lovey, Raymond G.. Related Products of 79707-11-2 The article mentions the following:

In search of a successor to the imidazol[1,2-a]pyridine I (X = CH, R = OCH2Ph, R1 = Me, R2 = CH2CN) (II) (Sch 28080), a compound that exhibits gastric antisecretory and cytoprotective properties, a series of imidazopyridines, e.g., I (X = CH; R = OCH2Ph; R1 = Me, NH2; R2 = Me, CH2CN, NH2) and of imidazopyrazines, e.g., I (X = N, R = OCH2Ph, R1 = Me, R2 = NH2) (III) were prepared In three of these potential successors of II, an amino group functions as a surrogate for the 3-cyanomethyl substituent of the prototype. In addition to an evaluation of the structure-activity relationships of a series of analogs of II, preliminary studies of the pharmacodynamics and metabolism of II were performed with the aid of cyano carbon labeled versions of the drug. II is well-absorbed and extensively metabolized; the major metabolite of II is the thiocyanate anion. A similar study performed on I (X = CH, R = OCH2Ph, R1 = Me, R2 = NH2) (IV), labeled at the 3-position with carbon-13 or carbon-14, revealed that IV, which has an antisecretory/cytoprotective profile comparable to that of II, is also metabolized to thiocyanate anion, although this must occur via a different mechanism. The potential sites of protonation of the pharmacol. similar IV and the structurally related imidazo[1,2-a]pyrazine III is discussed. Predictions based on charge d. and protonation product stabilities are presented. That N1 is the site of protonation in these analogs has been definitively demonstrated by x-ray crystal structure anal., which also unequivocally established the assigned imidazopyridine and imidazo[1,2-a]pyrazine ring structures.2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Related Products of 79707-11-2) was used in this study.

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Related Products of 79707-11-2 Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Knez, Damijan; Coquelle, Nicolas; Pislar, Anja; Zakelj, Simon; Jukic, Marko; Sova, Matej; Mravljak, Janez; Nachon, Florian; Brazzolotto, Xavier; Kos, Janko; Colletier, Jacques-Philippe; Gobec, Stanislav published their research in European Journal of Medicinal Chemistry on August 5 ,2018. The article was titled 《Multi-target-directed ligands for treating Alzheimer’s disease: Butyrylcholinesterase inhibitors displaying antioxidant and neuroprotective activities》.Computed Properties of C8H8N2O The article contains the following contents:

The limited clin. efficacy of current symptomatic treatment and minute effect on progression of Alzheimer’s disease has shifted the research focus from single targets towards multi-target-directed ligands. Here, a potent selective inhibitor of human butyrylcholinesterase was used as the starting point to develop a new series of multifunctional ligands. A focused library of derivatives was designed and synthesized that showed both butyrylcholinesterase inhibition and good antioxidant activity as determined by the DPPH assay. The crystal structure of compound 11 in complex with butyrylcholinesterase revealed the mol. basis for its low nanomolar inhibition of butyrylcholinesterase (Ki = 1.09±0.12 nM). In addition, compounds 8 and 11 show metal-chelating properties, and reduce the redox activity of chelated Cu2+ ions in a Cu-ascorbate redox system. Compounds 8 and 11 decrease intracellular levels of reactive oxygen species, and are not substrates of the active efflux transport system, as determined in Caco2 cells. Compound 11 also protects neuroblastoma SH-SY5Y cells from toxic Aβ1-42 species. These data indicate that compounds 8 and 11 are promising multifunctional lead ligands for treatment of Alzheimer’s disease. In the experiment, the researchers used 2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2Computed Properties of C8H8N2O)

2-Methylimidazo[1,2-a]pyridin-8-ol(cas: 79707-11-2) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
However, the application of imidazoles is not limited to the field of peptides and peptidomimetics. Computed Properties of C8H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem