8-(4-bromophenyl)-8-ethoxy-5-methyl-[1,2,4]oxadiazolo[3,4-c][1,4]thiazin-3(8H)-one

ID: ALA211204

Chembl Id: CHEMBL211204

PubChem CID: 11199490

Max Phase: Preclinical

Molecular Formula: C14H13BrN2O3S

Molecular Weight: 369.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC1(c2ccc(Br)cc2)SC=C(C)n2c1noc2=O

Standard InChI:  InChI=1S/C14H13BrN2O3S/c1-3-19-14(10-4-6-11(15)7-5-10)12-16-20-13(18)17(12)9(2)8-21-14/h4-8H,3H2,1-2H3

Standard InChI Key:  XCFCFGDFIJDQNG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA211204

   8-(4-Bromophenyl)-8-ethoxy-5-methyl-[1,2,4]oxadiazolo[3,4-c][1,4]thiazin-3-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: 369.24

Molecular Weight (Monoisotopic): 367.9830

AlogP: 3.40

#Rotatable Bonds: 3

Polar Surface Area: 57.26

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: -0.67

References

1. Carosati E, Cruciani G, Chiarini A, Budriesi R, Ioan P, Spisani R, Spinelli D, Cosimelli B, Fusi F, Frosini M, Matucci R, Gasparrini F, Ciogli A, Stephens PJ, Devlin FJ..  (2006)  Calcium channel antagonists discovered by a multidisciplinary approach.,  49  (17): [PMID:16913709] [10.1021/jm0604373]

2. Viale M, Cordazzo C, Cosimelli B, de Totero D, Castagnola P, Aiello C, Severi E, Petrillo G, Cianfriglia M, Spinelli D..  (2009)  Inhibition of MDR1 activity in vitro by a novel class of diltiazem analogues: toward new candidates.,  52  (2): [PMID:19093883] [10.1021/jm801195k]

3. Budriesi R, Cosimelli B, Ioan P, Ugenti MP, Carosati E, Frosini M, Fusi F, Spisani R, Saponara S, Cruciani G, Novellino E, Spinelli D, Chiarini A..  (2009)  L-Type calcium channel blockers: from diltiazem to 1,2,4-oxadiazol-5-ones via thiazinooxadiazol-3-one derivatives.,  52  (8): [PMID:19323482] [10.1021/jm801351u]

4. Carosati E, Ioan P, Barrano GB, Caccamese S, Cosimelli B, Devlin FJ, Severi E, Spinelli D, Superchi S, Budriesi R..  (2015)  Synthesis and L-type calcium channel blocking activity of new chiral oxadiazolothiazinones.,  92  [PMID:25596477] [10.1016/j.ejmech.2014.12.044]

5. Carosati E, Cosimelli B, Ioan P, Severi E, Katneni K, Chiu FC, Saponara S, Fusi F, Frosini M, Matucci R, Micucci M, Chiarini A, Spinelli D, Budriesi R..  (2016)  Understanding Oxadiazolothiazinone Biological Properties: Negative Inotropic Activity versus Cytochrome P450-Mediated Metabolism.,  59  (7): [PMID:26962886] [10.1021/acs.jmedchem.6b00030]

Source

Source(1):

• Scientific Literature