3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one

ID: ALA262597

Chembl Id: CHEMBL262597

Cas Number: 57601-14-6

PubChem CID: 5373273

Max Phase: Preclinical

Molecular Formula: C18H18O5

Molecular Weight: 314.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)/C=C/c2ccc(OC)c(OC)c2)c(O)c1

Standard InChI:  InChI=1S/C18H18O5/c1-21-13-6-7-14(16(20)11-13)15(19)8-4-12-5-9-17(22-2)18(10-12)23-3/h4-11,20H,1-3H3/b8-4+

Standard InChI Key:  SKTAHPCCLORHHM-XBXARRHUSA-N

Alternative Forms

1. Parent:

   

   ALA262597

   3-(3,4-Dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 314.34

Molecular Weight (Monoisotopic): 314.1154

AlogP: 3.31

#Rotatable Bonds: 6

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.10

CX Basic pKa: ┄

CX LogP: 3.76

CX LogD: 3.30

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: 0.32

References

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2. Ducki S, Rennison D, Woo M, Kendall A, Chabert JF, McGown AT, Lawrence NJ..  (2009)  Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: synthesis and biological evaluation of antivascular activity.,  17  (22): [PMID:19837593] [10.1016/j.bmc.2009.09.039]

3. Juvale K, Pape VF, Wiese M..  (2012)  Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein.,  20  (1): [PMID:22112540] [10.1016/j.bmc.2011.10.074]

4. Nam KY, Choi NS, Han CK, Ahn SK..  (2012)  Identification of chalcones as potent and selective PDE5A1 inhibitors.,  22  (12): [PMID:22607677] [10.1016/j.bmcl.2012.04.094]

5. Valdameri G, Gauthier C, Terreux R, Kachadourian R, Day BJ, Winnischofer SM, Rocha ME, Frachet V, Ronot X, Di Pietro A, Boumendjel A..  (2012)  Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: critical role of methoxylation in both inhibition potency and cytotoxicity.,  55  (7): [PMID:22449016] [10.1021/jm2016528]

6. Tran TD, Do TH, Tran NC, Ngo TD, Huynh TN, Tran CD, Thai KM..  (2012)  Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.,  22  (14): [PMID:22727643] [10.1016/j.bmcl.2012.05.112]

7. Rullah K, Mohd Aluwi MF, Yamin BM, Abdul Bahari MN, Wei LS, Ahmad S, Abas F, Ismail NH, Jantan I, Wai LK..  (2014)  Inhibition of prostaglandin E(2) production by synthetic minor prenylated chalcones and flavonoids: synthesis, biological activity, crystal structure, and in silico evaluation.,  24  (16): [PMID:25027933] [10.1016/j.bmcl.2014.06.061]

8. Borsari C, Santarem N, Torrado J, Olías AI, Corral MJ, Baptista C, Gul S, Wolf M, Kuzikov M, Ellinger B, Witt G, Gribbon P, Reinshagen J, Linciano P, Tait A, Costantino L, Freitas-Junior LH, Moraes CB, Bruno Dos Santos P, Alcântara LM, Franco CH, Bertolacini CD, Fontana V, Tejera Nevado P, Clos J, Alunda JM, Cordeiro-da-Silva A, Ferrari S, Costi MP..  (2017)  Methoxylated 2'-hydroxychalcones as antiparasitic hit compounds.,  126  [PMID:28064141] [10.1016/j.ejmech.2016.12.017]

9. Vijaya Bhaskar Reddy M, Hung HY, Kuo PC, Huang GJ, Chan YY, Huang SC, Wu SJ, Morris-Natschke SL, Lee KH, Wu TS..  (2017)  Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents.,  27  (7): [PMID:28256373] [10.1016/j.bmcl.2017.02.038]

10. Malik HS,Bilal A,Ullah R,Iqbal M,Khan S,Ahmed I,Krohn K,Saleem RSZ,Hussain H,Faisal A.  (2020)  Natural and Semisynthetic Chalcones as Dual FLT3 and Microtubule Polymerization Inhibitors.,  83  (10): [PMID:32975953] [10.1021/acs.jnatprod.0c00699]

11. Kayamba F, Malimabe T, Ademola IK, Pooe OJ, Kushwaha ND, Mahlalela M, van Zyl RL, Gordon M, Mudau PT, Zininga T, Shonhai A, Nyamori VO, Karpoormath R..  (2021)  Design and synthesis of quinoline-pyrimidine inspired hybrids as potential plasmodial inhibitors.,  217  [PMID:33744688] [10.1016/j.ejmech.2021.113330]

12. Qin HL, Zhang ZW, Lekkala R, Alsulami H, Rakesh KP..  (2020)  Chalcone hybrids as privileged scaffolds in antimalarial drug discovery: A key review.,  193  [PMID:32179331] [10.1016/j.ejmech.2020.112215]

Source

Source(1):

• Scientific Literature