10-(Chloroacetyl)-10H-phenothiazine

ID: ALA1651446

Cas Number: 786-50-5

PubChem CID: 69920

Max Phase: Preclinical

Molecular Formula: C14H10ClNOS

Molecular Weight: 275.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCl)N1c2ccccc2Sc2ccccc21

Standard InChI:  InChI=1S/C14H10ClNOS/c15-9-14(17)16-10-5-1-3-7-12(10)18-13-8-4-2-6-11(13)16/h1-8H,9H2

Standard InChI Key:  NVRFGQJNKQLUPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    7.3011   -4.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2998   -5.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0094   -5.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0074   -3.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7222   -4.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7258   -5.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4422   -5.5591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4348   -3.8998    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1557   -4.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1556   -5.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8727   -5.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5904   -5.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5866   -4.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8689   -3.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4458   -6.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7365   -6.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1585   -6.7876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7400   -7.6147    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  5  4  2  0
  4  1  1  0
  9 10  2  0
  5  6  1  0
 10 11  1  0
 11 12  2  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
 14  9  1  0
  1  2  2  0
  7 15  1  0
  5  8  1  0
 15 16  1  0
  6  7  1  0
 15 17  2  0
  7 10  1  0
 16 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1651446

   10-(Chloroacetyl)-10H-phenothiazine

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: 275.76

Molecular Weight (Monoisotopic): 275.0172

AlogP: 4.05

#Rotatable Bonds: 1

Polar Surface Area: 20.31

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.49

CX LogD: 3.49

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.73

Np Likeness Score: -0.97

References

1. Sarmiento GP, Vitale RG, Afeltra J, Moltrasio GY, Moglioni AG..  (2011)  Synthesis and antifungal activity of some substituted phenothiazines and related compounds.,  46  (1): [PMID:21093111] [10.1016/j.ejmech.2010.10.019]

2. Marcu A, Schurigt U, Müller K, Moll H, Krauth-Siegel RL, Prinz H..  (2016)  Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase.,  108  [PMID:26708110] [10.1016/j.ejmech.2015.11.023]

3. Vermelho AB, Capaci GR, Rodrigues IA, Cardoso VS, Mazotto AM, Supuran CT..  (2017)  Carbonic anhydrases from Trypanosoma and Leishmania as anti-protozoan drug targets.,  25  (5): [PMID:28161253] [10.1016/j.bmc.2017.01.034]

Source

Source(1):

• Scientific Literature