4-Benzothiazol-2-yl-phenol

ID: ALA47875

Chembl Id: CHEMBL47875

Cas Number: 6265-55-0

PubChem CID: 95745

Max Phase: Preclinical

Molecular Formula: C13H9NOS

Molecular Weight: 227.29

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4'-Hydroxyphenyl-Benzo[D]Thiazole | 4-(1,3-benzothiazol-2-yl)phenol|6265-55-0|4-(2-Benzothiazolyl)phenol|NSC33004|2-(p-Hydroxyphenyl)benzothiazole|4-(BENZO[D]THIAZOL-2-YL)PHENOL|Phenol, 4-(2-benzothiazolyl)-|CHEMBL47875|MLS000773814|4-(3H-1,3-benzothiazol-2-ylidene)cyclohexa-2,5-dien-1-one|MFCD01707773|SMR000364661|BRN 0163320|Phenol,4-(2-benzothiazolyl)-|NCIMech_000238|Phenol, p-2-benzothiazolyl-|SCHEMBL1346937|BDBM33932|cid_5351155|2-(4-hydroxyphenyl)benzothiazole|DTXSID60978211|ODMDLCWSMSFWCWShow More⌵

Canonical SMILES:  Oc1ccc(-c2nc3ccccc3s2)cc1

Standard InChI:  InChI=1S/C13H9NOS/c15-10-7-5-9(6-8-10)13-14-11-3-1-2-4-12(11)16-13/h1-8,15H

Standard InChI Key:  ODMDLCWSMSFWCW-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA47875

   4-(1,3-Benzothiazol-2-yl)phenol

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: 227.29

Molecular Weight (Monoisotopic): 227.0405

AlogP: 3.67

#Rotatable Bonds: 1

Polar Surface Area: 33.12

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.24

CX Basic pKa: 2.09

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 3

Heavy Atoms: 16

QED Weighted: 0.69

Np Likeness Score: -1.47

References

1. Stevens MF, McCall CJ, Lelieveld P, Alexander P, Richter A, Davies DE..  (1994)  Structural studies on bioactive compounds. 23. Synthesis of polyhydroxylated 2-phenylbenzothiazoles and a comparison of their cytotoxicities and pharmacological properties with genistein and quercetin.,  37  (11): [PMID:8201603] [10.1021/jm00037a020]

2. Wells G, Bradshaw TD, Diana P, Seaton A, Shi DF, Westwell AD, Stevens MF..  (2000)  Antitumour benzothiazoles. Part 10: the synthesis and antitumour activity of benzothiazole substituted quinol derivatives.,  10  (5): [PMID:10743960] [10.1016/s0960-894x(00)00027-5]

3. Wells G, Berry JM, Bradshaw TD, Burger AM, Seaton A, Wang B, Westwell AD, Stevens MF..  (2003)  4-Substituted 4-hydroxycyclohexa-2,5-dien-1-ones with selective activities against colon and renal cancer cell lines.,  46  (4): [PMID:12570375] [10.1021/jm020984y]

4. PubChem BioAssay data set, 

5. Ha YM, Park JY, Park YJ, Park D, Choi YJ, Kim JM, Lee EK, Han YK, Kim JA, Lee JY, Moon HR, Chung HY..  (2011)  Synthesis and biological activity of hydroxy substituted phenyl-benzo[d]thiazole analogues for antityrosinase activity in B16 cells.,  21  (8): [PMID:21397499] [10.1016/j.bmcl.2011.02.064]

6. Khan KM, Rahim F, Halim SA, Taha M, Khan M, Perveen S, Zaheer-Ul-Haq, Mesaik MA, Iqbal Choudhary M..  (2011)  Synthesis of novel inhibitors of β-glucuronidase based on benzothiazole skeleton and study of their binding affinity by molecular docking.,  19  (14): [PMID:21684753] [10.1016/j.bmc.2011.05.052]

7. Bandyopadhyay P, Sathe M, Ponmariappan S, Sharma A, Sharma P, Srivastava AK, Kaushik MP..  (2011)  Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents.,  21  (24): [PMID:22047695] [10.1016/j.bmcl.2011.10.034]

8. Capes A, Patterson S, Wyllie S, Hallyburton I, Collie IT, McCarroll AJ, Stevens MF, Frearson JA, Wyatt PG, Fairlamb AH, Gilbert IH..  (2012)  Quinol derivatives as potential trypanocidal agents.,  20  (4): [PMID:22264753] [10.1016/j.bmc.2011.12.018]

9. PubChem BioAssay data set, 

10. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• AstraZeneca Deposited Data