10477-72-2

Basic information

• Product Name: phenacid
• Synonyms: phenacid;4-[Bis(2-chloroethyl)amino]benzeneacetic acid;CB-1331;NSC-71964;p-[Bis(2-chloroethyl)amino]phenylacetic acid;Phenylacetic acid mustard;Phenylacetic acid Mustard-d8
• CAS NO: 10477-72-2
• Molecular Formula: C₁₂H₁₅Cl₂NO₂
• Molecular Weight: 276.18
• Mol File: 10477-72-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 125°C (rough estimate)
• Flash Point: 89.6°C
• Appearance: /
• Density: 1.2884 (rough estimate)
• Vapor Pressure: 0.418mmHg at 25°C
• Refractive Index: 1.6070 (estimate)
• CAS DataBase Reference: phenacid(CAS DataBase Reference)
• NIST Chemistry Reference: phenacid(10477-72-2)
• EPA Substance Registry System: phenacid(10477-72-2)

Safety Data

• Hazardous Substances Data: 10477-72-2(Hazardous Substances Data)

Usage

Description

Phenylacetic Mustard, also known as Phenacid, is a nitrogen mustard analog and the active metabolite of Chlorambucil (C325050). It is characterized by its clastogenic activity and ability to induce chromosome delay.

Uses

Used in Pharmaceutical Industry:
Phenylacetic Mustard is used as a chemotherapeutic agent for its clastogenic activity and ability to induce chromosome delay, making it a valuable compound in the treatment of various cancers.
Used in Cancer Treatment:
Phenylacetic Mustard is utilized as an anticancer agent, particularly in the treatment of solid malignancies. Its clastogenic activity and chromosome delay induction properties contribute to its effectiveness in combating cancer cells and potentially improving patient outcomes when used in combination with other therapeutic approaches.

Safety Profile

Poison by intraperitoneal route. Experimental reproductive effects. Mutation data reported. Whenheated to decomposition it emits toxic fumes of Clí and NOx.

InChI:InChI=1/C8H6ClO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,1H2

Upstream product

• 30716-00-8 4-phenylacetic acid N-oxide 
• 5445-26-1 ETHYL 4-NITROPHENYLACETATE 
• 104-03-0 4-nitrobenzeneacetic acid 
• 31386-35-3 p-phenylessigsaeureethylester 
• 39552-81-3 methyl p-aminophenylacetate 
• 500590-36-3 2-(4-(N,N-bis(2-chloroethyl)amino)phenyl)acetaldehyde 
• 5438-70-0 ethyl (4-amino-3,5-dibromophenyl)acetate 
• 174579-27-2 {4-[Bis-(2-hydroxy-ethyl)-amino]-phenyl}-acetic acid tert-butyl ester 
• 174579-31-8 (4-aminophenyl)acetic acid tert-butyl ester 
• 29704-38-9 (4-nitrophenyl)acetic acid tert-butyl ester 
• 1197-55-3 4-aminophenylacetic acid 
• 119054-10-3 {4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-acetic acid tert-butyl ester 
• 219313-75-4 {4-[bis-(2-hydroxy-ethyl)-amino]-phenyl}-acetic acid ethyl ester 

Downstream Products

• 86377-69-7 3β-hydroxy-13α-amino-13,17-seco-5α-androstan-17-oic-13,17-lactamphenyl> acetate 
• 83100-47-4 ClPh-ONP 
• 24141-90-0 {4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-acetic acid (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 3546-10-9 phenesterine 
• 24199-63-1 {4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-acetic acid (3S,8S,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 90360-47-7 N--L-alanine-3β-hydroxy-5-androsten-17-one ester 
• 90360-46-6 N--L-alanine-3β-hydroxy-5-cholesten ester 
• 53039-95-5 p-phenylacetyl chloride hydrochloride 
• 115769-35-2 p-Methoxybenzyl 3-O-[p-[N,N-bis(2-chloroethyl)amino]-phenylacetyl] cholate 
• 79567-53-6 (2-Acetoxymethyl-1,3-diacetoxy-2-propyl)amide of 4-phenylacetic acid 
• 77931-56-7 (5-Hydroxymethyl-2,2-pentamethylene-1,3-dioxan-5-yl)amide of 4--phenylacetic acid 

Relevant articles and documents

Synthesis of androstene oxime-nitrogen mustard bioconjugates as potent antineoplastic agents

In the present study, synthesis and antineoplastic activity of phenylacetic acid and benzoic acid nitrogen mustard conjugates of various steroidal oximes are reported for the first time. The conjugation was achieved through a more stable oxime-ester linkage and the resulting newly synthesized conjugates were evaluated in vitro on various human cancer cell lines for cytotoxicity. The extent of their alkylating activity was investigated by the in vitro colorimetric 4-(p-nitrobenzyl)pyridine (NBP) assay. The 17E-steroidal oxime-benzoic acid mustard ester 3β-acetoxy-17E-[p-(N,N-bis(2-chloroethyl)amino)]benzoyloxyimino-androst-5-ene (8) emerged as the most potent conjugate having significant cytotoxicity on most of the NCI 60-cell lines. Outstanding growth inhibition was observed on the IGROV1 ovarian cancer cell line with GI50?=?0.937?μM. In general, the D-ring derived androstene oxime-nitrogen mustard conjugates were found to possess better antineoplastic activity over a variety of cancer cells in comparison to those derived from other rings of the steroid skeleton.

Nitrogen Mustard Derivatives

The disclosure includes compounds of Formula (1): wherein X1, X2, Q, Z, R1, and R2 are defined herein. Also disclosed is a method for treating a neoplastic disease or an immune disease with these compounds.

Benzimidazole derivatives

Disclosed are compounds represented by the following chemical formula (I) and pharmacologically acceptable salts thereof which are novel compounds useful as anticancer agents, antiviral agents or antimicrobial agents. STR1