TDI-11861: Difference between revisions

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;

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Revision as of 18:41, 7 March 2023

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, Thomas; Ferreira, Jacob; Ghanem, Lubna; Buck, Hannes; Steegborn, Clemens; Myers, Robert W.; Meinke, Peter T.; Levin, Lonny R.; Buck, Jochen (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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
^ 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. 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. doi:10.1038/s41467-023-36119-6. PMID 36788210.
^ Balbach M, et al. Soluble Adenylyl Cyclase (sAC) Inhibitors and Uses Thereof. WO 2022/232259

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[1] Rossetti, Thomas; Ferreira, Jacob; Ghanem, Lubna; Buck, Hannes; Steegborn, Clemens; Myers, Robert W.; Meinke, Peter T.; Levin, Lonny R.; Buck, Jochen (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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[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. 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. doi:10.1038/s41467-023-36119-6. PMID 36788210.

[4] Balbach M, et al. Soluble Adenylyl Cyclase (sAC) Inhibitors and Uses Thereof. WO 2022/232259

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-'''TDI-11861''' is a chemical compound which acts as a selective inhibitor of [[soluble adenylyl cyclase]] (sAC).<ref>{{cite journal | vauthors = Miller M, Rossetti T, Ferreira J, Ghanem L, Balbach M, Kaur N, Levin LR, Buck J, Kehr M, Coquille S, van den Heuvel J, Steegborn C, Fushimi M, Finkin-Groner E, Myers RW, Kargman S, Liverton NJ, Huggins DJ, Meinke PT | display-authors = 6 | title = Design, Synthesis, and Pharmacological Evaluation of Second-Generation Soluble Adenylyl Cyclase (sAC, ADCY10) Inhibitors with Slow Dissociation Rates | journal = Journal of Medicinal Chemistry | volume = 65 | issue = 22 | pages = 15208–15226 | date = November 2022 | doi = 10.1021/acs.jmedchem.2c01133 | pmid = 36346696 | s2cid = 253395810 }}</ref> 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.<ref>{{cite journal | vauthors = Balbach M, Rossetti T, Ferreira J, Ghanem L, Ritagliati C, Myers RW, Huggins DJ, Steegborn C, Miranda IC, Meinke PT, Buck J, Levin LR | display-authors = 6 | title = On-demand male contraception via acute inhibition of soluble adenylyl cyclase | journal = Nature Communications | volume = 14 | issue = 1 | pages = 637 | date = February 2023 | doi = 10.1038/s41467-023-36119-6 | pmid = 36788210 }}</ref><ref>[https://patentscope.wipo.int/search/docs2/pct/WO2022232259/pdf/3o6h2aGteuMvl7uC2yVSPzO0-sxjnxSPlUkCAPz1M1txaMdVIvmgxcu5Wq6SMFNFvkHruzPYzH7_e6c0glIrb-8b4OYNI_8Zjd_cz55BpKlUtdfk1ZCEBue2hw6_oEfE?docId=id00000069315041&filename=WO2022232259-PAMPH-20221103-5041.pdf Balbach M, et al. Soluble Adenylyl Cyclase (sAC) Inhibitors and Uses Thereof. WO 2022/232259]</ref>
+'''TDI-11861''' is a chemical compound which acts as a potent <ref>{{cite journal |last1=Rossetti |first1=Thomas |last2=Ferreira |first2=Jacob |last3=Ghanem |first3=Lubna |last4=Buck |first4=Hannes |last5=Steegborn |first5=Clemens |last6=Myers |first6=Robert W. |last7=Meinke |first7=Peter T. |last8=Levin |first8=Lonny R. |last9=Buck |first9=Jochen |title=Assessing potency and binding kinetics of soluble adenylyl cyclase (sAC) inhibitors to maximize therapeutic potential |journal=Frontiers in Physiology |date=28 September 2022 |volume=13 |pages=1013845 |doi=10.3389/fphys.2022.1013845}}</ref> and selective inhibitor of [[soluble adenylyl cyclase]] (sAC).<ref>{{cite journal | vauthors = Miller M, Rossetti T, Ferreira J, Ghanem L, Balbach M, Kaur N, Levin LR, Buck J, Kehr M, Coquille S, van den Heuvel J, Steegborn C, Fushimi M, Finkin-Groner E, Myers RW, Kargman S, Liverton NJ, Huggins DJ, Meinke PT | display-authors = 6 | title = Design, Synthesis, and Pharmacological Evaluation of Second-Generation Soluble Adenylyl Cyclase (sAC, ADCY10) Inhibitors with Slow Dissociation Rates | journal = Journal of Medicinal Chemistry | volume = 65 | issue = 22 | pages = 15208–15226 | date = November 2022 | doi = 10.1021/acs.jmedchem.2c01133 | pmid = 36346696 | s2cid = 253395810 }}</ref> 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.<ref>{{cite journal | vauthors = Balbach M, Rossetti T, Ferreira J, Ghanem L, Ritagliati C, Myers RW, Huggins DJ, Steegborn C, Miranda IC, Meinke PT, Buck J, Levin LR | display-authors = 6 | title = On-demand male contraception via acute inhibition of soluble adenylyl cyclase | journal = Nature Communications | volume = 14 | issue = 1 | pages = 637 | date = February 2023 | doi = 10.1038/s41467-023-36119-6 | pmid = 36788210 }}</ref><ref>[https://patentscope.wipo.int/search/docs2/pct/WO2022232259/pdf/3o6h2aGteuMvl7uC2yVSPzO0-sxjnxSPlUkCAPz1M1txaMdVIvmgxcu5Wq6SMFNFvkHruzPYzH7_e6c0glIrb-8b4OYNI_8Zjd_cz55BpKlUtdfk1ZCEBue2hw6_oEfE?docId=id00000069315041&filename=WO2022232259-PAMPH-20221103-5041.pdf Balbach M, et al. Soluble Adenylyl Cyclase (sAC) Inhibitors and Uses Thereof. WO 2022/232259]</ref>
 == See also ==