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Usage

Uses

Used in Pharmaceutical Industry:
1H-Indazol-4-ol, 3-aminois used as a building block for the synthesis of various pharmaceuticals and organic compounds. Its versatile reactivity and pharmacological properties make it a valuable component in the development of new drugs with diverse biological activities.
Used in Medicinal Chemistry Research:
1H-Indazol-4-ol, 3-aminois used as a pharmacophore in medicinal chemistry research for the development of novel drugs. Its potential role as a pharmacophore allows for the exploration of its diverse biological activities and the creation of new therapeutic agents.

Upstream product

• 140675-43-0 2-Fluoro-6-hydroxybenzonitrile 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of indazole arylsulfonamides as allosteric CC-chemokine receptor 4 (CCR4) antagonists

A series of indazole arylsulfonamides were synthesized and examined as human CCR4 antagonists. Methoxy- or hydroxyl- containing groups were the more potent indazole C4 substituents. Only small groups were tolerated at C5, C6, or C7, with the C6 analogues being preferred. The most potent N3-substituent was 5-chlorothiophene-2-sulfonamide. N1 meta-substituted benzyl groups possessing an α-amino-3-[(methylamino)acyl]- group were the most potent N1-substituents. Strongly basic amino groups had low oral absorption in vivo. Less basic analogues, such as morpholines, had good oral absorption; however, they also had high clearance. The most potent compound with high absorption in two species was analogue 6 (GSK2239633A), which was selected for further development. Aryl sulfonamide antagonists bind to CCR4 at an intracellular allosteric site denoted site II. X-ray diffraction studies on two indazole sulfonamide fragments suggested the presence of an important intramolecular interaction in the active conformation.

Aminoindazole derivatives

A compound of the formula (I): STR1 wherein W1 and W2 each independently is a hydrogen atom or a STR2 group wherein Y is a n-C1-6 alkylene group or a n-C1-6 alkylene group having a C1-6 alkyl group substituent; and R1 and R2 each independently is a hydrogen atom or a C1-6 alkyl group, and STR3 group in STR4 group may form a saturated heterocyclic ring selected from the group consisting of morpholino, pyrrolidino, piperidino, homopiperidino and piperazino groups, and the saturated heterocyclic ring except the morpholino group may have at least one C1-4 alkyl group, hydroxyl group or halogen atom as a substituent; Z1 is a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, an amino group, a C1-3 alkyl group or a methoxy group; Z2 is a hydrogen atom or an amino group; when W1 and W2 are both hydrogen atoms, Z1 is a hydroxyl group or an iodine atom and Z2 is hydrogen atom, or Z1 and Z2 are both amino groups; when Z1 and Z2 are both hydrogen atoms, the STR5 group in either W1 or W2 is a morpholino group; when Z1 is a chlorine atom, a hydroxyl group, an iodine atom, a methyl group or a methoxy group, Z2 is a hydrogen atom; when Z1 is an amino group, Z2 is a hydrogen atom or an amino group; when Z1 is a methyl group, a methoxy group or an amino group, Z1 is in the 5-position; when Z1 is an iodine atom, Z1 is in the 5- or 7-position; and when Z1 and Z2 are both amino groups, Z1 and Z2 are in the 5- and 7-positions; and the physiologically acceptable acid addition salt thereof which compounds have pharmaceutical utility, e.g.: treating inflammation.