(S)-7-Methoxy-8-(3-{4-[5-(4-methyl-piperazin-1-yl)-1H-benzoimidazol-2-yl]-phenoxy}-propoxy)-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one

ID: ALA184059

PubChem CID: 10326157

Max Phase: Preclinical

Molecular Formula: C34H38N6O4

Molecular Weight: 594.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OCCCOc1ccc(-c3nc4ccc(N5CCN(C)CC5)cc4[nH]3)cc1)N=C[C@@H]1CCCN1C2=O

Standard InChI:  InChI=1S/C34H38N6O4/c1-38-13-15-39(16-14-38)24-8-11-28-30(19-24)37-33(36-28)23-6-9-26(10-7-23)43-17-4-18-44-32-21-29-27(20-31(32)42-2)34(41)40-12-3-5-25(40)22-35-29/h6-11,19-22,25H,3-5,12-18H2,1-2H3,(H,36,37)/t25-/m0/s1

Standard InChI Key:  AQHPQTMEIVSAKL-VWLOTQADSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA184059

   7-methoxy-8-(3-4-[6-(4-methylhexahydro-1-pyrazinyl)-1H-benzo [d]imidazol-2-yl]phenoxypropoxy)-(11aS)-2,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-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: 594.72

Molecular Weight (Monoisotopic): 594.2955

AlogP: 5.16

#Rotatable Bonds: 9

Polar Surface Area: 95.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.17

CX Basic pKa: 7.87

CX LogP: 4.05

CX LogD: 3.44

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.27

Np Likeness Score: -0.59

References

1. Kamal A, Ramulu P, Srinivas O, Ramesh G, Kumar PP..  (2004)  Synthesis of C8-linked pyrrolo[2,1-c][1,4]benzodiazepine-benzimidazole conjugates with remarkable DNA-binding affinity.,  14  (18): [PMID:15324909] [10.1016/j.bmcl.2004.06.069]

2. Rettig M, Kamal A, Ramu R, Mikolajczak J, Weisz K..  (2009)  Spectroscopic and calorimetric studies on the DNA recognition of pyrrolo[2,1-c][1,4]benzodiazepine hybrids.,  17  (2): [PMID:19056283] [10.1016/j.bmc.2008.11.033]

Source

Source(1):

• Scientific Literature