TDI-11861

TDI-11861
Identifiers
	IUPAC name [(3R)-4-[2-[2-[[3-(2-amino-6-chloropyrimidin-4-yl)-1-(difluoromethyl)pyrazol-4-yl]methyl]phenoxy]ethyl]morpholin-3-yl]methanol;
CAS Number	2857049-72-8;
PubChem CID	166101565;
Chemical and physical data
Formula	C22H25ClF2N6O3
Molar mass	494.93 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1COC[C@H](N1CCOC2=CC=CC=C2CC3=CN(N=C3C4=CC(=NC(=N4)N)Cl)C(F)F)CO;
	InChI InChI=1S/C22H25ClF2N6O3/c23-19-10-17(27-22(26)28-19)20-15(11-31(29-20)21(24)25)9-14-3-1-2-4-18(14)34-8-6-30-5-7-33-13-16(30)12-32/h1-4,10-11,16,21,32H,5-9,12-13H2,(H2,26,27,28)/t16-/m1/s1; Key:XVGSKZXXLKUEIO-MRXNPFEDSA-N;

TDI-11861 is a chemical compound which acts as a potent ^[1] and selective inhibitor of soluble adenylyl cyclase (sAC).^[2] In animal studies it reversibly inhibits sperm motility, producing temporary infertility without hormonal side effects. While TDI-11861 is at an early developmental stage and is unlikely to be developed for medical uses in humans itself, it represents an important proof of concept which may potentially lead to the development of future male contraceptive drugs.^[3]^[4]

References

^ Rossetti T, Ferreira J, Ghanem L, Buck H, Steegborn C, Myers RW, et al. (28 September 2022). "Assessing potency and binding kinetics of soluble adenylyl cyclase (sAC) inhibitors to maximize therapeutic potential". Frontiers in Physiology. 13: 1013845. doi:10.3389/fphys.2022.1013845. PMC 9554468. PMID 36246105.
^ Miller M, Rossetti T, Ferreira J, Ghanem L, Balbach M, Kaur N, et al. (November 2022). "Design, Synthesis, and Pharmacological Evaluation of Second-Generation Soluble Adenylyl Cyclase (sAC, ADCY10) Inhibitors with Slow Dissociation Rates". Journal of Medicinal Chemistry. 65 (22): 15208–15226. doi:10.1021/acs.jmedchem.2c01133. PMC 9866367. PMID 36346696. S2CID 253395810.
^ Balbach M, Rossetti T, Ferreira J, Ghanem L, Ritagliati C, Myers RW, et al. (February 2023). "On-demand male contraception via acute inhibition of soluble adenylyl cyclase". Nature Communications. 14 (1): 637. Bibcode:2023NatCo..14..637B. doi:10.1038/s41467-023-36119-6. PMC 9929232. PMID 36788210.
^ WO 2022/232259, Balbach M, et al., "Soluble Adenylyl Cyclase (sAC) Inhibitors and Uses Thereof", published 3 November 2022, assigned to Cornell University and Tri-Institutional Therapeutics Discovery Institute, Inc.

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[1] Rossetti T, Ferreira J, Ghanem L, Buck H, Steegborn C, Myers RW, et al. (28 September 2022). "Assessing potency and binding kinetics of soluble adenylyl cyclase (sAC) inhibitors to maximize therapeutic potential". Frontiers in Physiology. 13: 1013845. doi:10.3389/fphys.2022.1013845. PMC 9554468. PMID 36246105.

[2] Miller M, Rossetti T, Ferreira J, Ghanem L, Balbach M, Kaur N, et al. (November 2022). "Design, Synthesis, and Pharmacological Evaluation of Second-Generation Soluble Adenylyl Cyclase (sAC, ADCY10) Inhibitors with Slow Dissociation Rates". Journal of Medicinal Chemistry. 65 (22): 15208–15226. doi:10.1021/acs.jmedchem.2c01133. PMC 9866367. PMID 36346696. S2CID 253395810.

[3] Balbach M, Rossetti T, Ferreira J, Ghanem L, Ritagliati C, Myers RW, et al. (February 2023). "On-demand male contraception via acute inhibition of soluble adenylyl cyclase". Nature Communications. 14 (1): 637. Bibcode:2023NatCo..14..637B. doi:10.1038/s41467-023-36119-6. PMC 9929232. PMID 36788210.

[4] WO 2022/232259, Balbach M, et al., "Soluble Adenylyl Cyclase (sAC) Inhibitors and Uses Thereof", published 3 November 2022, assigned to Cornell University and Tri-Institutional Therapeutics Discovery Institute, Inc.

[1]

[2]

[3]

[4]

Identifiers

IUPAC name [(3R)-4-[2-[2-[[3-(2-amino-6-chloropyrimidin-4-yl)-1-(difluoromethyl)pyrazol-4-yl]methyl]phenoxy]ethyl]morpholin-3-yl]methanol
CAS Number	2857049-72-8
PubChem CID	166101565
Chemical and physical data
Formula	C₂₂H₂₅ClF₂N₆O₃
Molar mass	494.93 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1COC[C@H](N1CCOC2=CC=CC=C2CC3=CN(N=C3C4=CC(=NC(=N4)N)Cl)C(F)F)CO
InChI InChI=1S/C22H25ClF2N6O3/c23-19-10-17(27-22(26)28-19)20-15(11-31(29-20)21(24)25)9-14-3-1-2-4-18(14)34-8-6-30-5-7-33-13-16(30)12-32/h1-4,10-11,16,21,32H,5-9,12-13H2,(H2,26,27,28)/t16-/m1/s1 Key:XVGSKZXXLKUEIO-MRXNPFEDSA-N

TDI-11861

See also

References