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Chemistry

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Also known as: Zn-c3, 2376146-48-2, 9j13xu96z1, 1-[(7r)-7-ethyl-7-hydroxy-5,6-dihydrocyclopenta[b]pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-prop-2-enylpyrazolo[3,4-d]pyrimidin-3-one, 1-[(7r)-7-ethyl-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-(prop-2-en-1-yl)-1,2-dihydro-3h-pyrazolo[3,4-d]pyrimidin-3-one, 3h-pyrazolo(3,4-d)pyrimidin-3-one, 1-((7r)-7-ethyl-6,7-dihydro-7-hydroxy-5h-cyclopenta(b)pyridin-2-yl)-1,2-dihydro-6-((4-(4-methyl-1-piperazinyl)phenyl)amino)-2-(2-propen-1-yl)-
Molecular Formula
C29H34N8O2
Molecular Weight
526.6  g/mol
InChI Key
OXTSYWDBUVRXFF-GDLZYMKVSA-N
FDA UNII
9J13XU96Z1

Azenosertib
Wee1 Inhibitor ZN-c3 is an inhibitor of the tyrosine kinase Wee1 (Wee1-like protein kinase; Wee1A kinase; WEE1hu) with potential antineoplastic sensitizing activity. Although the exact mechanism of action by which this agent inhibits Wee1 has yet to be disclosed, upon administration of ZN-c3, this agent targets and inhibits Wee1. Inhibition of Wee1 promotes both premature mitosis and a prolonged mitotic arrest leading to cell death in susceptible tumor cells, such as p53-deficient or mutated human cancers that lack the G1 checkpoint, upon treatment with DNA-damaging chemotherapeutic agents. Unlike normal cells, most p53-deficient or mutated human cancers lack the G1 checkpoint as p53 is the key regulator of the G1 checkpoint and these cells rely on the G2 checkpoint for DNA repair to damaged cells. Annulment of the G2 checkpoint may therefore make p53-deficient tumor cells more vulnerable to antineoplastic agents and enhance their cytotoxic effect. Overexpression of Wee1 occurs in several cancer types and high expression of Wee1 is associated with poor outcomes. Wee1 phosphorylates Cdc2 in the Cdc2/cyclin B (CDK1/cyclin B) complex which blocks progression from G2 into mitosis; it negatively regulates the G2 checkpoint by disallowing entry into mitosis in response to DNA damage.
1 2D Structure

Azenosertib

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[(7R)-7-ethyl-7-hydroxy-5,6-dihydrocyclopenta[b]pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-prop-2-enylpyrazolo[3,4-d]pyrimidin-3-one
2.1.2 InChI
InChI=1S/C29H34N8O2/c1-4-14-36-27(38)23-19-30-28(31-21-7-9-22(10-8-21)35-17-15-34(3)16-18-35)33-26(23)37(36)24-11-6-20-12-13-29(39,5-2)25(20)32-24/h4,6-11,19,39H,1,5,12-18H2,2-3H3,(H,30,31,33)/t29-/m1/s1
2.1.3 InChI Key
OXTSYWDBUVRXFF-GDLZYMKVSA-N
2.1.4 Canonical SMILES
CCC1(CCC2=C1N=C(C=C2)N3C4=NC(=NC=C4C(=O)N3CC=C)NC5=CC=C(C=C5)N6CCN(CC6)C)O
2.1.5 Isomeric SMILES
CC[C@]1(CCC2=C1N=C(C=C2)N3C4=NC(=NC=C4C(=O)N3CC=C)NC5=CC=C(C=C5)N6CCN(CC6)C)O
2.2 Other Identifiers
2.2.1 UNII
9J13XU96Z1
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Zn-c3

2. 2376146-48-2

3. 9j13xu96z1

4. 1-[(7r)-7-ethyl-7-hydroxy-5,6-dihydrocyclopenta[b]pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-prop-2-enylpyrazolo[3,4-d]pyrimidin-3-one

5. 1-[(7r)-7-ethyl-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-(prop-2-en-1-yl)-1,2-dihydro-3h-pyrazolo[3,4-d]pyrimidin-3-one

6. 3h-pyrazolo(3,4-d)pyrimidin-3-one, 1-((7r)-7-ethyl-6,7-dihydro-7-hydroxy-5h-cyclopenta(b)pyridin-2-yl)-1,2-dihydro-6-((4-(4-methyl-1-piperazinyl)phenyl)amino)-2-(2-propen-1-yl)-

7. Azenosertib

8. Znc3

9. Unii-9j13xu96z1

10. Schembl21333380

11. Gtpl11731

12. Ex-a6113

13. Nsc837398

14. Nsc-837398

15. Compound 16 [pmid: 34423975]

16. Hy-132295

17. 05j

2.4 Create Date
2019-11-02
3 Chemical and Physical Properties
Molecular Weight 526.6 g/mol
Molecular Formula C29H34N8O2
XLogP33.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count7
Exact Mass526.28047236 g/mol
Monoisotopic Mass526.28047236 g/mol
Topological Polar Surface Area101 Ų
Heavy Atom Count39
Formal Charge0
Complexity875
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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