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

ID: ALA192989

Chembl Id: CHEMBL192989

PubChem CID: 11849743

Max Phase: Preclinical

Molecular Formula: C14H13BrN2O3S

Molecular Weight: 369.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCO[C@@]1(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/t14-/m0/s1

Standard InChI Key:  XCFCFGDFIJDQNG-AWEZNQCLSA-N

Alternative Forms

1. Parent:

   

   ALA192989

   (8S)-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. Budriesi R, Carosati E, Chiarini A, Cosimelli B, Cruciani G, Ioan P, Spinelli D, Spisani R..  (2005)  A new class of selective myocardial calcium channel modulators. 2. Role of the acetal chain in oxadiazol-3-one derivatives.,  48  (7): [PMID:15801835] [10.1021/jm0493414]

2. 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]

3. Carosati E, Budriesi R, Ioan P, Cruciani G, Fusi F, Frosini M, Saponara S, Gasparrini F, Ciogli A, Villani C, Stephens PJ, Devlin FJ, Spinelli D, Chiarini A..  (2009)  Stereoselective behavior of the functional diltiazem analogue 1-[(4-chlorophenyl)sulfonyl]-2-(2-thienyl)pyrrolidine, a new L-type calcium channel blocker.,  52  (21): [PMID:19831392] [10.1021/jm9008696]

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]

Source

Source(1):

• Scientific Literature