1-(4-Nitro-phenyl)-3-(2,2,4,4-tetramethyl-thiochroman-6-yl)-thiourea

ID: ALA7075

Cas Number: 361483-66-1

PubChem CID: 9844020

Max Phase: Phase

Molecular Formula: C20H23N3O2S2

Molecular Weight: 401.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Sheta-2 | Sheta2 | NSC-721689 | NSC-726189 | SHETA-2 | SHETA2 | SHetA2|Sheta-2|NSC-726189|NSC-721689|S886C92NJ7|361483-66-1|CHEMBL7075|UNII-S886C92NJ7|N-(3,4-Dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-N'-(4-nitrophenyl)thiourea|Thiourea, N-(3,4-dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-N'-(4-nitrophenyl)-|1-(4-nitrophenyl)-3-(2,2,4,4-tetramethylthiochroman-6-yl)thiourea|SCHEMBL13417328|BDBM50539102|NSC726189|1-(4-nitrophenyl)-3-(2,2,4,4-tetramethyl-3H-thiochromen-6-yl)thioShow More⌵

Canonical SMILES:  CC1(C)CC(C)(C)c2cc(NC(=S)Nc3ccc([N+](=O)[O-])cc3)ccc2S1

Standard InChI:  InChI=1S/C20H23N3O2S2/c1-19(2)12-20(3,4)27-17-10-7-14(11-16(17)19)22-18(26)21-13-5-8-15(9-6-13)23(24)25/h5-11H,12H2,1-4H3,(H2,21,22,26)

Standard InChI Key:  FWWKIYPMUZVMQG-UHFFFAOYSA-N

Molfile:  

Thiourea, N-(3,4-dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-N'-(4-...
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   29.4766  -11.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4793  -10.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4821  -11.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1283   -9.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1283   -8.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4793   -7.4884    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.8304   -8.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8304   -9.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3666   -8.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3639   -6.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7774   -7.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4263   -8.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4263   -9.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7774  -10.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0753  -10.6085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7244   -9.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7244   -8.2684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3733   -7.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3733   -5.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0224   -5.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6713   -5.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6713   -7.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0224   -8.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3203   -5.1484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3203   -3.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9694   -5.9285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3733  -10.6085    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  7  6  1  0
  8  7  1  0
  2  8  1  0
  7  9  1  0
  7 10  1  0
  5 11  2  0
 11 12  1  0
 13 12  2  0
 14 13  1  0
  4 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 22 21  1  0
 23 22  2  0
 18 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  2  0
 16 27  2  0
M  CHG  2  24   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA7075

   SHETA-2

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 401.56

Molecular Weight (Monoisotopic): 401.1232

AlogP: 5.96

#Rotatable Bonds: 3

Polar Surface Area: 67.20

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.63

CX Basic pKa: ┄

CX LogP: 6.03

CX LogD: 6.03

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.38

Np Likeness Score: -1.19

References

1. Liu S, Brown CW, Berlin KD, Dhar A, Guruswamy S, Brown D, Gardner GJ, Birrer MJ, Benbrook DM..  (2004)  Synthesis of flexible sulfur-containing heteroarotinoids that induce apoptosis and reactive oxygen species with discrimination between malignant and benign cells.,  47  (4): [PMID:14761202] [10.1021/jm030346v]

2. Liu S, Louie MC, Rajagopalan V, Zhou G, Ponce E, Nguyen T, Green L..  (2015)  Synthesis and evaluation of the diarylthiourea analogs as novel anti-cancer agents.,  25  (6): [PMID:25701251] [10.1016/j.bmcl.2015.01.042]

3. Gnanasekaran KK, Benbrook DM, Nammalwar B, Thavathiru E, Bunce RA, Berlin KD..  (2015)  Synthesis and evaluation of second generation Flex-Het scaffolds against the human ovarian cancer A2780 cell line.,  96  [PMID:25880346] [10.1016/j.ejmech.2015.03.070]

4. Watts FM, Pouland T, Bunce RA, Berlin KD, Benbrook DM, Mashayekhi M, Bhandari D, Zhou D..  (2018)  Activity of oxygen-versus sulfur-containing analogs of the Flex-Het anticancer agent SHetA2.,  158  [PMID:30245396] [10.1016/j.ejmech.2018.09.036]

5. Nammalwar B, Bunce RA, Berlin KD, Benbrook DM, Toal C..  (2019)  Synthesis and biological evaluation of SHetA2 (NSC-721689) analogs against the ovarian cancer cell line A2780.,  170  [PMID:30878829] [10.1016/j.ejmech.2019.03.010]

6. Gnanasekaran KK, Pouland T, Bunce RA, Darrell Berlin K, Abuskhuna S, Bhandari D, Mashayekhi M, Zhou DH, Benbrook DM..  (2020)  Tetrahydroquinoline units in flexible heteroarotinoids (Flex-Hets) convey anti-cancer properties in A2780 ovarian cancer cells.,  28  (1): [PMID:31831296] [10.1016/j.bmc.2019.115244]

7. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Clinical Candidates