(E)-2-(3-Methylbut-2-en-1-yl)-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl 3-Phenylpropanoate

ID: ALA4518474

PubChem CID: 142412524

Max Phase: Preclinical

Molecular Formula: C28H35BO4

Molecular Weight: 446.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=CCc1cc(/C=C/B2OC(C)(C)C(C)(C)O2)ccc1OC(=O)CCc1ccccc1

Standard InChI:  InChI=1S/C28H35BO4/c1-21(2)12-15-24-20-23(18-19-29-32-27(3,4)28(5,6)33-29)13-16-25(24)31-26(30)17-14-22-10-8-7-9-11-22/h7-13,16,18-20H,14-15,17H2,1-6H3/b19-18+

Standard InChI Key:  UIJXVKIETDMBCE-VHEBQXMUSA-N

Molfile:  

 
     RDKit          2D

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   38.8273  -14.5084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4112  -15.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7032  -15.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9993  -15.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2917  -15.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2906  -16.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0030  -16.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7076  -16.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5354  -14.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5352  -13.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8274  -12.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8272  -12.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1198  -13.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4518474

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 446.40

Molecular Weight (Monoisotopic): 446.2628

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#RO5 Violations (Lipinski): ┄

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References

1. Verma K, Zang T, Penning TM, Trippier PC..  (2019)  Potent and Highly Selective Aldo-Keto Reductase 1C3 (AKR1C3) Inhibitors Act as Chemotherapeutic Potentiators in Acute Myeloid Leukemia and T-Cell Acute Lymphoblastic Leukemia.,  62  (7): [PMID:30836001] [10.1021/acs.jmedchem.9b00090]

2. Adeniji, Adegoke O AO and 5 more authors.  2011-03-01  Discovery of substituted 3-(phenylamino)benzoic acids as potent and selective inhibitors of type 5 17β-hydroxysteroid dehydrogenase (AKR1C3).  [PMID:21277203]

3. Adeniji, Adegoke O AO and 6 more authors.  2012-03-08  Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N-phenyl-aminobenzoates and their structure-activity relationships.  [PMID:22263837]

4. Brožič, Petra and 7 more authors.  2012-09-13  Selective inhibitors of aldo-keto reductases AKR1C1 and AKR1C3 discovered by virtual screening of a fragment library.  [PMID:22881866]

5. Hendriks, Christine M M and 7 more authors.  2015-10-15  Pentafluorosulfanyl-containing flufenamic acid analogs: Syntheses, properties and biological activities.  [PMID:26372652]

6. Pippione, Agnese C AC and 12 more authors.  2017-10-20  Hydroxytriazole derivatives as potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors discovered by bioisosteric scaffold hopping approach.  [PMID:28881288]

7. Endo, Satoshi S and 16 more authors.  2017-10-26  Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.  [PMID:28976752]

8. Pippione, Agnese Chiara AC and 15 more authors.  2018-04-25  Potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors based on the benzoisoxazole moiety: application of a bioisosteric scaffold hopping approach to flufenamic acid.  [PMID:29602039]

Source

Source(1):

• Scientific Literature