21443-96-9Relevant articles and documents
Efficient synthesis of 7-substituted or 3,7-disubstituted 1H-indazoles
Cottyn, Betty,Vichard, Dominique,Terrier, Fran?ois,Nioche, Pierre,Raman
, p. 1203 - 1206 (2007)
This work reports on the synthesis of the novel indazole scaffolds 7-OTf-1H-indazole (trifluoromethanesulfonic acid 1H-indazol-7-yl ester), 7-iodo-1H-indazole and 3-bromo-7-iodo-1H-indazole. These new compounds are potent building blocks in divergent syntheses of indazoles via palladium cross-coupling reactions. Georg Thieme Verlag Stuttgart.
Synthesis of new α-amino-1H indazolyl-phosphonate derivatives: Crystal structure, Hirshfeld surface analysis and DFT studies
Ihammi, Aziz,Chigr, Mohammed,Ketatni, El Mostafa,Saadi, Mohamed,El Ammari, Lahcen,Rakib, El Mostapha
, (2020)
A new α-amino-1H Indazolyl-phosphonates derivative 3a–e were synthesized and subjected to solid state characterization by single-crystal X-ray diffraction analysis, and to study their NMR and Hirshfeld surface analysis. The P atom exhibits tetrahedral geometry involving two O-ethyl groups, a C atom and a double-bonded O atom. The P–C bond has an approximately staggered conformation, with the aniline and substituted groups in gauche positions with respect to the P[dbnd]O double bond. The molecules are arranged as centrosymmetric or pseudocentrosymmetric dimers connected by two N–H?O[dbnd]P hydrogen bonds and also by C–H … π interaction in the case of structures 3a–e, which are responsible for the formation and stability of the molecular assemblies. Hirshfeld surface analysis (dnorm surface and two-dimensional (2D) fingerprint plots) revealed the nature of intermolecular contacts. The most important contributions for the crystal packing are from H?H, H?C/C?H, O?H/H?O, and H?N/N?H interactions. In addition, frontier molecular orbitals and Molecular Electrostatic Potential map of the compounds was produced by using the optimized structures.
Synthesis and molecular modeling studies of N-Hydroxyindazolecarboximidamides as novel indoleamine 2,3-Dioxygenase 1 (IDO1) inhibitors
Lee, Dong-Ho,Lee, Joo-Youn,Jeong, Jieun,Kim, Miok,Lee, Kyung Won,Jang, Eunseo,Ahn, Sunjoo,Lee, Chang Hoon,Hwang, Jong Yeon
, (2017/12/06)
Indoleamine 2,3-dioxygenase 1 (IDO1) is an immunosuppressive enzyme that is highly overexpressed in various cancer cells and antigen-presenting cells. It has emerged as an attractive therapeutic target for cancer immunotherapy, which has prompted high interest in the development of small-molecule inhibitors. To discover novel IDO1 inhibitors, we designed and synthesized a series of N-hydroxyindazolecarboximidamides. Among the compounds synthesized, compound 8a inhibited both tryptophan depletion and kynurenine production through the IDO1 enzyme. Molecular docking studies revealed that 8a binds to IDO1 with the same binding mode as the analog, epacadostat (INCB24360). Here, we report the synthesis and biological evaluation of these hydroxyindazolecarboximidamides and present the molecular docking study of 8a with IDO1.
