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Chemical Compound Review:

INDAZOLE 1H-indazole

Synonyms: BENZPYRAZOL, ISOINDAZONE, Isoindazole, BENZPYRAZOLE, Benzopyrazole, ...

Iwakubo, M. et al., Harada, H. et al., Shirtcliff, L.D. et al., Takami, A. et al.

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High impact information on Isoindazole

Lewis-acid promoted "coarctate" cyclization of 10 2-(phenylazo)benzonitrile derivatives furnishes the isoindazole ring system in ca. 65-95% yield [1].
The choice of the linker substructure was shown to be an important factor for the 1H-indazole analogues to inhibit the chemotaxis of cells [2].
During this study, we found that the cell-free enzyme inhibitory potential of Rho kinase inhibitors having the 1H-indazole scaffold did not necessarily correlate with their inhibitory potential toward the chemotaxis of cultured cells [2].
In this study, the detailed structure-activity relationship of 1H-indazole analogues was studied [2].
Optimization of the 1H-indazole inhibitors with respect to the in vitro inhibition of monocyte chemotaxis induced by MCP-1 was carried out [2].

Associations of Isoindazole with other chemical compounds

We identified several potent platforms for developing the Rho kinase inhibitors, namely, pyridine, 1H-indazole, isoquinoline, and phthalimide [3].

Gene context of Isoindazole

Within this series, use of the 1H-indazole ring as an aromatic moiety led to a substantial increase of the activity; the 1H-indazolylcarboxamides 54, 57, 97, and 102 showed potent 5-HT3 receptor antagonistic activity [4].

References

Synthesis of 2H-indazoles via Lewis acid promoted cyclization of 2-(phenylazo)benzonitriles. Shirtcliff, L.D., Rivers, J., Haley, M.M. J. Org. Chem. (2006) [Pubmed]
Design and synthesis of Rho kinase inhibitors (II). Iwakubo, M., Takami, A., Okada, Y., Kawata, T., Tagami, Y., Ohashi, H., Sato, M., Sugiyama, T., Fukushima, K., Iijima, H. Bioorg. Med. Chem. (2007) [Pubmed]
Design and synthesis of Rho kinase inhibitors (I). Takami, A., Iwakubo, M., Okada, Y., Kawata, T., Odai, H., Takahashi, N., Shindo, K., Kimura, K., Tagami, Y., Miyake, M., Fukushima, K., Inagaki, M., Amano, M., Kaibuchi, K., Iijima, H. Bioorg. Med. Chem. (2004) [Pubmed]
Development of potent serotonin-3 (5-HT3) receptor antagonists. II. Structrue-activity relationships of N-(1-benzyl-4-methylhexahydro-1H-1,4- diazepin-6-yl)carboxamides. Harada, H., Morie, T., Hirokawa, Y., Terauchi, H., Fujiwara, I., Yoshida, N., Kato, S. Chem. Pharm. Bull. (1995) [Pubmed]

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