130198-76-4

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-(4-(BIS(2-HYDROXYETHYL)AMINO)PHENYL)BUTYRATE is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical structure allows it to be a key component in the development of new medications.
Used in Personal Care Industry:
In the personal care industry, METHYL 4-(4-(BIS(2-HYDROXYETHYL)AMINO)PHENYL)BUTYRATE is used as an ingredient in skin creams and lotions. It is valued for its emollient and moisturizing properties, which contribute to the skin's health and appearance.
Used in Organic Synthesis and Research:
METHYL 4-(4-(BIS(2-HYDROXYETHYL)AMINO)PHENYL)BUTYRATE is also utilized in the field of organic synthesis and research. Its versatile chemical properties make it a valuable compound for exploring new chemical reactions and developing innovative applications.

InChI:InChI=1/C15H23NO4/c1-20-15(19)4-2-3-13-5-7-14(8-6-13)16(9-11-17)10-12-18/h5-8,17-18H,2-4,9-12H2,1H3

Upstream product

• 75-21-8 oxirane 
• 20637-09-6 methyl 4-(4-aminophenyl)butanoate 
• 15118-60-2 4-(4-aminophenyl)butyric Acid 
• 205759-94-0 methyl 4-(p-aminophenyl)butyrate 
• 62-53-3 aniline 
• 103-84-4 Acetanilid 
• 5473-15-4 4-(4-acetamidophenyl)-4-oxobutanoic acid 
• 20637-02-9 methyl 4-(4-nitrophenyl)butanoate 

Downstream Products

• 130031-42-4 Acridin-9-yl-(3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propyl)-amine 
• 90393-37-6 N,N-bis(2-chloroethyl)-4-(3-isocyanatopropyl)phenylamine 
• 129787-13-9 3-[4-[N,N-bis(2-chloroethyl)amino]-phenyl]-propylamine 
• 305-03-3 chlorambucil 
• 269402-54-2 N/[3-(dimethylamino)propyl]-4-{4-[bis(2-chloroethyl)amino]phenyl}-butyramide 
• 17981-81-6 chlorambucil chloride 
• 79481-83-7 methyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate 

Relevant academic research and scientific papers

A process for synthesizing phenylbutyric acid nitrogen mustard antineoplastic agent

The invention relates to a synthesis process of an antineoplastic drug chlorambucil. The synthesis process comprises the following steps: (1) amino protection reaction; (2) acylation reaction; (3) reduction reaction; (4) carboxyl protection reaction; (5) substitution reaction; (6) chlorination reaction; and (7) deprotection reaction. According to the synthesis process, the amino group is protected by use of acetic anhydride, and then acylation, reduction, carboxyl protection, substitution, chlorination and aqueous hydrochloric acid solution hydrolysis are performed to obtain the chlorambucil. The synthesis process of the antineoplastic drug chlorambucil has the characteristics of low cost, mild reaction conditions, low toxicity, convenience in process operation, and suitability for industrial production.

Synthesis and pharmacokinetic profile of a quaternary ammonium derivative of chlorambucil, a potential anticancer drug for the chemotherapy of chondrosarcoma

As a part of our targeting program based on the affinity of the quaternary ammonium moiety for cartilage, our objective was to develop more selective anticancer drugs towards chondrosarcoma that would concentrate in this malignant cartilaginous tissue and so improve the therapeutic index through a reduction of side effects. For this purpose we have synthesized and labeled with 14C a quaternary ammonium (QA) derivative of chlorambucil. Biological studies performed in rats showed that [14C]-CQA and [ 14C]-chlorambucil exhibited different pharmacokinetic profiles. The blood elimination of [14C]-CQA was faster than that of parent compound. [14C]-CQA was principally excreted by the fecal way. However, until 15 min after administration, levels of radioactivity were measured in cartilaginous tissues of rats given [14C]-CQA which was not the case for the rats which had received [14C]-chlorambucil. Although rates of radioactivity were quantified only during 15 min, these results prove that the functionalization of chlorambucil by a quaternary ammonium group allows the molecule to be carried selectively to cartilaginous tissues.

DNA-Directed Alkylating Agents. 3. Structure-Activity Relationships for Acridine-Linked Aniline Mustards: Consequences of Varying the Length of the Linker Chain

Four series of acridine-linked aniline mustards have been prepared and evaluated for in vitro cytotoxicity, in vivo antitumor activity, and DNA cross-linking ability.The anilines were attached to the DNA-intercalating acridine chromophores by link groups (-O-, -CH2-, -S-, and -SO2-) of widely varying electronic properties, providing four series of widely differing mustard reactivity where the alkyl chain linking the acridine and mustard moieties was varied from two to five carbons.Relationships were sought between chain length and biological properties.Within eachseries, increasing the chain length did not alter the reactivity of the alkylating moiety but did appear to position it differently on the DNA, since cross-linking ability (measured by agarose gel assay) altered with chain length, being maximal with the C4 analogue.The in vivo antitumor activities of the compounds dependend to some extent on the reactivity of the mustard, with the least reactive SO2 compounds being inactive.However, DNA-targeting did appear to allow the use of less reactive mustards, since the S-linked acridine mustards showed significant activity whereas the parent S-mustard did not.Within each active series, the most active compound was the C4 homologue, suggesting some relationship between activity and extent of DNA alkylation.