2N-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-1H-3-pyrrolyl]-4-{4-[4-di(2-chloroethyl)aminophenylcarboxamido]-1-methyl-1H-2-pyrrolylcarboxamido}-1-methyl-1H-2-pyrrolecarboxamide hydrochloride

ID: ALA545612

Chembl Id: CHEMBL545612

Cas Number: 118438-45-2

PubChem CID: 6918104

Max Phase: Preclinical

Molecular Formula: C32H39Cl3N10O4

Molecular Weight: 697.63

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tallimustine | Tallimustine hydrochloride|JWV8AC9E4V|FCE-24517|UNII-JWV8AC9E4V|118438-45-2|N-(5-(((3-Amino-3-iminopropyl)amino)carbonyl)-1-methyl-1H-pyrrol-3-yl)-4-(((4-((4-(bis(2-chloroethyl)amino)benzoyl)amino)-1-methyl-1H-pyrrol-2-yl)carbonyl)amino)-1-methyl-1H-pyrrole-2-carboxamide hydrochloride|1H-Pyrrole-2-carboxamide, N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-[[4-[bis(2-chloroethyl)amino]benzoyl]amino]-1- methyl-1H-pyrrol-2-yl]carbonyl]amino]-1-methyl-,Show More⌵

Canonical SMILES:  Cl.Cn1cc(NC(=O)c2cc(NC(=O)c3cc(NC(=O)c4ccc(N(CCCl)CCCl)cc4)cn3C)cn2C)cc1C(=O)NCCC(=N)N

Standard InChI:  InChI=1S/C32H38Cl2N10O4.ClH/c1-41-18-22(14-25(41)30(46)37-11-8-28(35)36)39-32(48)27-16-23(19-43(27)3)40-31(47)26-15-21(17-42(26)2)38-29(45)20-4-6-24(7-5-20)44(12-9-33)13-10-34;/h4-7,14-19H,8-13H2,1-3H3,(H3,35,36)(H,37,46)(H,38,45)(H,39,48)(H,40,47);1H

Standard InChI Key:  BLSOATWWAGIRGE-UHFFFAOYSA-N

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: 697.63

Molecular Weight (Monoisotopic): 696.2455

AlogP: 3.80

#Rotatable Bonds: 15

Polar Surface Area: 184.30

Molecular Species: BASE

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 12.56

CX LogP: 2.41

CX LogD: -0.01

Aromatic Rings: 4

Heavy Atoms: 48

QED Weighted: 0.06

Np Likeness Score: -0.64

References

1. Baraldi PG, Beria I, Cacciari B, Cozzi P, Franzetti C, Mongelli N, Romagnoli R, Spalluto G.  (1996)  Synthesis and antitumor activity of novel distamycin derivatives,  6  (11): [10.1016/0960-894X(96)00204-1]

2. Baraldi PG, Beria I, Cacciari B, Capolongo L, Cozzi P, Mongelli N, Romagnoli R, Spalluto G.  (1996)  Structure-activity relationship of novel tallimustine derivatives: synthesis and antitumor activity,  6  (11): [10.1016/0960-894X(96)00205-3]

3. D'Allessio R, Geroni C, Biasoli G, Pesenti E, Grandi M, Mongelli N.  (1994)  Structure-activity relationship of novel distamycin a derivatives : synthesis and antitumor activity,  4  (12): [10.1016/S0960-894X(01)80515-1]

4. Cozzi P, Beria I, Caldarelli M, Capolongo L, Geroni C, Mazzini S, Ragg E..  (2000)  Phenyl sulfur mustard derivatives of distamycin A.,  10  (15): [PMID:10937717] [10.1016/s0960-894x(00)00295-x]

5. Baraldi PG, Romagnoli R, Beria I, Cozzi P, Geroni C, Mongelli N, Bianchi N, Mischiati C, Gambari R..  (2000)  Synthesis and antitumor activity of new benzoheterocyclic derivatives of distamycin A.,  43  (14): [PMID:10893305] [10.1021/jm9911229]

6. Cozzi P, Beria I, Biasoli G, Caldarelli M, Capolongo L, Geroni C, Mongelli N.  (1997)  Novel phenyl nitrogen mustard and half-mustard derivatives of amidino-modified distamycin,  7  (23): [10.1016/S0960-894X(97)10120-2]

7. Arcamone FM, Animati F, Barbieri B, Configliacchi E, D'Alessio R, Geroni C, Giuliani FC, Lazzari E, Menozzi M, Mongelli N..  (1989)  Synthesis, DNA-binding properties, and antitumor activity of novel distamycin derivatives.,  32  (4): [PMID:2590277] [10.1021/jm00124a008]

Source

Source(1):

• Scientific Literature