N-Benzyl-1-(1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)-methanamine

ID: ALA3799981

Chembl Id: CHEMBL3799981

PubChem CID: 127046200

Max Phase: Preclinical

Molecular Formula: C20H21ClN2

Molecular Weight: 324.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(CNCc2ccccc2)c(C)n1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C20H21ClN2/c1-15-12-18(14-22-13-17-6-4-3-5-7-17)16(2)23(15)20-10-8-19(21)9-11-20/h3-12,22H,13-14H2,1-2H3

Standard InChI Key:  LPLUTGPMNSANQX-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3799981

   ---

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: 324.86

Molecular Weight (Monoisotopic): 324.1393

AlogP: 5.04

#Rotatable Bonds: 5

Polar Surface Area: 16.96

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 8.48

CX LogP: 5.22

CX LogD: 4.11

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: -1.73

References

1. Bhakta S, Scalacci N, Maitra A, Brown AK, Dasugari S, Evangelopoulos D, McHugh TD, Mortazavi PN, Twist A, Petricci E, Manetti F, Castagnolo D..  (2016)  Design and Synthesis of 1-((1,5-Bis(4-chlorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)-4-methylpiperazine (BM212) and N-Adamantan-2-yl-N'-((E)-3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine (SQ109) Pyrrole Hybrid Derivatives: Discovery of Potent Antitubercular Agents Effective against Multidrug-Resistant Mycobacteria.,  59  (6): [PMID:26907951] [10.1021/acs.jmedchem.6b00031]

2. Masci D, Hind C, Islam MK, Toscani A, Clifford M, Coluccia A, Conforti I, Touitou M, Memdouh S, Wei X, La Regina G, Silvestri R, Sutton JM, Castagnolo D..  (2019)  Switching on the activity of 1,5-diaryl-pyrrole derivatives against drug-resistant ESKAPE bacteria: Structure-activity relationships and mode of action studies.,  178  [PMID:31202995] [10.1016/j.ejmech.2019.05.087]

3. Touitou M, Manetti F, Ribeiro CM, Pavan FR, Scalacci N, Zrebna K, Begum N, Semenya D, Gupta A, Bhakta S, McHugh TD, Senderowitz H, Kyriazi M, Castagnolo D..  (2020)  Improving the Potency of N-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria.,  11  (5): [PMID:32435364] [10.1021/acsmedchemlett.9b00515]

Source

Source(1):

• Scientific Literature