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Synopsis

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Also known as: 1639417-53-0, Rp6530, Tenalisib [inn], 2261hh611h, (s)-2-(1-((7h-purin-6-yl)amino)propyl)-3-(3-fluorophenyl)-4h-chromen-4-one, 3-(3-fluorophenyl)-2-[(1s)-1-(7h-purin-6-ylamino)propyl]chromen-4-one

Molecular Formula

C₂₃H₁₈FN₅O₂

Molecular Weight

415.4 g/mol

InChI Key

HDXDQPRPFRKGKZ-INIZCTEOSA-N

FDA UNII

2261HH611H

Tenalisib is an orally active, highly selective, small molecule inhibitor of the delta and gamma isoforms of phosphoinositide-3 kinase (PI3K) with potential immunomodulating and antineoplastic activities. Upon administration, tenalisib inhibits the PI3K delta and gamma isoforms and prevents the activation of the PI3K/AKT-mediated signaling pathway. This may lead to a reduction in cellular proliferation in PI3K delta/gamma-expressing tumor cells. In addition, this agent modulates inflammatory responses through various mechanisms, including the inhibition of both the release of reactive oxygen species (ROS) from neutrophils and tumor necrosis factor (TNF)-alpha activity. Unlike other isoforms of PI3K, the delta and gamma isoforms are overexpressed primarily in hematologic malignancies and in inflammatory and autoimmune diseases. By selectively targeting these isoforms, PI3K signaling in normal, non-neoplastic cells is minimally impacted or not affected at all, which minimizes the side effect profile for this agent.

1 2D Structure

Tenalisib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(3-fluorophenyl)-2-[(1S)-1-(7H-purin-6-ylamino)propyl]chromen-4-one

2.1.2 InChI

InChI=1S/C23H18FN5O2/c1-2-16(29-23-19-22(26-11-25-19)27-12-28-23)21-18(13-6-5-7-14(24)10-13)20(30)15-8-3-4-9-17(15)31-21/h3-12,16H,2H2,1H3,(H2,25,26,27,28,29)/t16-/m0/s1

2.1.3 InChI Key

HDXDQPRPFRKGKZ-INIZCTEOSA-N

2.1.4 Canonical SMILES

CCC(C1=C(C(=O)C2=CC=CC=C2O1)C3=CC(=CC=C3)F)NC4=NC=NC5=C4NC=N5

2.1.5 Isomeric SMILES

CC[C@@H](C1=C(C(=O)C2=CC=CC=C2O1)C3=CC(=CC=C3)F)NC4=NC=NC5=C4NC=N5

2.2 Other Identifiers

2.2.1 UNII

2261HH611H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-(3-fluorophenyl)-2-((1s)-1-(7h-purin-6-ylamino)propyl)chromen-4-one

2. Rp6530

2.3.2 Depositor-Supplied Synonyms

1. 1639417-53-0

2. Rp6530

3. Tenalisib [inn]

4. 2261hh611h

5. (s)-2-(1-((7h-purin-6-yl)amino)propyl)-3-(3-fluorophenyl)-4h-chromen-4-one

6. 3-(3-fluorophenyl)-2-[(1s)-1-(7h-purin-6-ylamino)propyl]chromen-4-one

7. Rp-6530

8. 3-(3-fluorophenyl)-2-((1s)-1-((7h-purin-6-yl)amino)propyl)-4h-1-benzopyran-4-one

9. 4h-1-benzopyran-4-one, 3-(3-fluorophenyl)-2-((1s)-1-(9h-purin-6-ylamino)propyl)-

10. Tenalisib (rp6530)

11. 3-(3-fluorophenyl)-2-((1s)-1-(7h-purin-6-ylamino)propyl)chromen-4-one

12. Rp6530, Tenalisib

13. Tenalisib [who-dd]

14. Gtpl9907

15. Chembl4297584

16. Schembl16279460

17. Schembl21828463

18. Unii-2261hh611h

19. Bcp25998

20. Ex-a2699

21. Bdbm50512870

22. Nsc803014

23. Rp6530rp6530

24. S8672

25. Akos037645008

26. Ccg-268828

27. Cs-6375

28. Db15295

29. Nsc-803014

30. Rp 6530

31. As-56118

32. Hy-17645

33. A16799

34. C73162

35. A857570

36. Q27253617

37. (s)-2-(1-((9h-purin-6-yl)amino)propyl)-3-(3-fluorophenyl)-4h-chromen-4-one

38. 3-(3-fluorophenyl)-2-[(1s)-1-[(9h-purin-6-yl)amino]propyl]-4h-chromen-4-one

39. 1693773-94-2

2.4 Create Date

2014-12-22

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₁₈FN₅O₂
Molecular Weight	415.4 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	415.14445300 g/mol
Monoisotopic Mass	415.14445300 g/mol
Topological Polar Surface Area	92.8 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	704
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Phosphoinositide-3 Kinase Inhibitors

Agents that inhibit PHOSPHOINOSITIDE-3 KINASE activity. (See all compounds classified as Phosphoinositide-3 Kinase Inhibitors.)

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