Imidazopyridazine

Imidazopyridazine
Identifiers
CAS Number	imidazo[4,5-c]pyridazine: 327-02-6; imidazo[4,5-d]pyridazine: 273-00-7; imidazo[1,2-b]pyridazine: 766-55-2;
3D model (JSmol)	imidazo[4,5-c]pyridazine: Interactive image; imidazo[4,5-d]pyridazine: Interactive image; imidazo[1,2-b]pyridazine: Interactive image;
ChEMBL	imidazo[4,5-d]pyridazine: ChEMBL3144350;
ChemSpider	imidazo[4,5-c]pyridazine: 9204993; imidazo[4,5-d]pyridazine: 4521598; imidazo[1,2-b]pyridazine: 120366;
EC Number	imidazo[1,2-b]pyridazine: 806-512-8;
PubChem CID	imidazo[4,5-c]pyridazine: 11029819; imidazo[4,5-d]pyridazine: 5370875; imidazo[1,2-b]pyridazine: 136599;
UNII	imidazo[1,2-b]pyridazine: HC9C5RH4HC;
CompTox Dashboard (EPA)	imidazo[4,5-d]pyridazine: DTXSID40418680;
	InChI imidazo[4,5-c]pyridazine: InChI=1S/C5H4N4/c1-2-8-9-5-4(1)6-3-7-5/h1-3H,(H,6,7,9) Key: MJQSRSOTRPMVKB-UHFFFAOYSA-N; imidazo[4,5-d]pyridazine: InChI=1S/C5H4N4/c1-4-5(2-9-8-1)7-3-6-4/h1-3H,(H,6,7) Key: UWZYICUGNHLGSA-UHFFFAOYSA-N; imidazo[1,2-b]pyridazine: InChI=1S/C6H5N3/c1-2-6-7-4-5-9(6)8-3-1/h1-5H Key: VTVRXITWWZGKHV-UHFFFAOYSA-N;
	SMILES imidazo[4,5-c]pyridazine: C1=CN=NC2=C1NC=N2; imidazo[4,5-d]pyridazine: C1=C2C(=CN=N1)N=CN2; imidazo[1,2-b]pyridazine: C1=CC2=NC=CN2N=C1;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Imidazopyridazine is a heterocyclic compound containing fused imidazole and pyridazine rings.^[1]^[2] The fusion of these two heterocyclic rings can yield three different isomers, namely imidazo[4,5-c]pyridazine and imidazo[4,5-d]pyridazine, both of which contain two nitrogen atoms in each ring. A third possible structure is imidazo[1,2-b]pyridazine, in which one nitrogen atom is shared between the imidazole and pyridazine rings (and hence contains one less nitrogen atom and therefore is non-isomeric).^[1]

Ponatinib, a medication used to treat chronic myeloid leukemia, contains an imidazo[1,2-b]pyridazine substructure. Examples of experimental drugs containing this ring system include darigabat (an imidazo[4,5-c]pyridazine), as well as GBLD-345 and SRI-42127 (both imidazo[1,2-b]pyridazines).

References

1 2 Malik MS, Alshareef HF, Alfaidi KA, Ather H, Abduljaleel Z, Hussein EM, et al. (January 2024). "Exploring the untapped pharmacological potential of imidazopyridazines". RSC Advances. 14 (6): 3972–3984. Bibcode:2024RSCAd..14.3972M. doi:10.1039/d3ra07280k. PMC 10823362. PMID 38288152.
↑ Volpi G, Laurenti E, Rabezzana R (June 2024). "Imidazopyridine Family: Versatile and Promising Heterocyclic Skeletons for Different Applications". Molecules. 29 (11). Basel, Switzerland: 2668. doi:10.3390/molecules29112668. PMC 11173518. PMID 38893542.

[Malik_2024-1] 1 2 Malik MS, Alshareef HF, Alfaidi KA, Ather H, Abduljaleel Z, Hussein EM, et al. (January 2024). "Exploring the untapped pharmacological potential of imidazopyridazines". RSC Advances. 14 (6): 3972–3984. Bibcode:2024RSCAd..14.3972M. doi:10.1039/d3ra07280k. PMC 10823362. PMID 38288152.

[Volpi_2024-2] Volpi G, Laurenti E, Rabezzana R (June 2024). "Imidazopyridine Family: Versatile and Promising Heterocyclic Skeletons for Different Applications". Molecules. 29 (11). Basel, Switzerland: 2668. doi:10.3390/molecules29112668. PMC 11173518. PMID 38893542.

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