15944-88-4

Basic information

• Product Name: 4-[bis(2-chloroethyl)amino]benzoyl chloride
• CAS NO: 15944-88-4
• Molecular Formula: C₁₁H₁₂Cl₃NO
• Molecular Weight: 280.5781
• Mol File: 15944-88-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 394.1°C at 760 mmHg
• Flash Point: 192.2°C
• Density: 1.338g/cm³
• Vapor Pressure: 2.02E-06mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: 4-[bis(2-chloroethyl)amino]benzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[bis(2-chloroethyl)amino]benzoyl chloride(15944-88-4)
• EPA Substance Registry System: 4-[bis(2-chloroethyl)amino]benzoyl chloride(15944-88-4)

Safety Data

• Hazardous Substances Data: 15944-88-4(Hazardous Substances Data)

Upstream product

• 1141-37-3 4-{bis(2-chloroethyl)amino}benzoic acid 

Downstream Products

• 77444-64-5 4-[Bis-(2-chloro-ethyl)-amino]-benzoic acid 5-carbamoyl-1H-imidazol-4-yl ester 
• 118438-45-2 tallimustine 
• 179983-39-2 1-methyl-4-[p-bis(2-chloroethyl)aminobenzamido]-imidazole-2-carboxylic acid 
• 177409-16-4 1-methyl-4-<4-bis(2-chloroethyl)aminophenylamido>pyrazole-5-carboxylic acid 
• 288625-59-2 ethyl 1-methyl-4-[p-bis(2-chloroethyl)aminobenzamido]-imidazole-2-carboxylate 
• 294174-59-7 5-{4-[bis-(2-chloro-ethyl)-amino]-benzoylamino}-1H-indole-2-carboxylic acid ethyl ester 
• 294174-60-0 5-{4-[bis-(2-chloro-ethyl)-amino]-benzoylamino}-1-methyl-1H-indole-2-carboxylic acid ethyl ester 
• 4251-79-0 {4-[Bis-(2-chloro-ethyl)-amino]-benzoylamino}-acetic acid 

Relevant articles and documents

In Vitro Cytotoxicity of GC Sequence Directed Alkylating Agents Related to Distamycin

Imidazole containing analogues 7, 10, and 17 of distamycin wherein the C-terminus contain a dimethylamino moiety have been shown to selectively bind to the minor groove of GC-rich sequences. Accordingly, these agents were employed as vectors for the deliv

Structure-activity relationship of a series of C-terminus modified aminoalkyl, diaminoalkyl- and anilino-containing analogues of the benzoic acid mustard distamycin derivative tallimustine: Synthesis, DNA binding and cytotoxicity studies

As part of our investigations into the design of more cytotoxic analogues of the experimental anticancer drug tallimustine, 1, C-terminus modified aminoalkyl-, 2a-c, diaminoalkyl-, 3, and anilino-containing, 4, derivatives have been synthesized. Compounds 2a-c differ by 2, 3, or 4 methylene units in the C-terminus, respectively. Results from an ethidium displacement study on poly(dA-dT), poly(dG-dC), calf thymus DNA and T4 coliphage DNA showed that compounds 2-4 interact in the minor groove of the polynucleotides with a preference for poly(dA-dT) over poly(dG-dC). Compound 4 bound more weakly to the DNAs than 2a-c and 3. Using a CD dilution assay compounds 2a-c and 3 were demonstrated to bind irreversibly to calf thymus DNA. The sequence selectivity by which compounds 2-4 alkylate DNA was demonstrated using a Tag polymerase stop assay. All the compounds alkylated preferentially at the 3'-purine residue in a 5'-TTTTGPu-3' sequence (Pu = A or G). This observed sequence specificity is similar to that of tallimustine and a related compound 5. At an equimolar concentration the aminoalkyl compounds 2a-c (2b > 2a > 2c), and diaminoalkyl compound 3 were more efficient at alkylating these sequences than the anilino compound 4. Following a one hour exposure of human chronic myeloid leukemia K562 cells, compounds 2b and 3 have lower IC50, values (1.64 μM and 3.03 μM, respectively) than tallimustine (5 μM) and similar values to a related compound 5 (2.2 μM) The order of cytotoxicity for all the compounds is 2b > 5 > 3 > 2a > 1 > 2c = 4. These results indicate that the cytotoxicities of these compounds are related to their relative ability to alkylate the consensus DNA binding sequence.