20637-02-9

Basic information

• Product Name: 4-Nitrobenzenebutanoic acid methyl ester
• Synonyms: 4-(4-Nitrophenyl)butanoic acid methyl ester;4-Nitrobenzenebutanoic acid methyl ester;4-Nitrobenzenebutyric acid methyl ester
• CAS NO: 20637-02-9
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.2252
• Mol File: 20637-02-9.mol

Chemical Properties

• Boiling Point: 344.1°Cat760mmHg
• Flash Point: 150.2°C
• Appearance: /
• Density: 1.193g/cm³
• Vapor Pressure: 6.74E-05mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Nitrobenzenebutanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrobenzenebutanoic acid methyl ester(20637-02-9)
• EPA Substance Registry System: 4-Nitrobenzenebutanoic acid methyl ester(20637-02-9)

Safety Data

• Hazardous Substances Data: 20637-02-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13NO4/c1-16-11(13)4-2-3-9-5-7-10(8-6-9)12(14)15/h5-8H,2-4H2,1H3

Upstream product

• 67-56-1 methanol 
• 5600-62-4 4-(4-nitrophenyl)butanoic acid 
• 186581-53-3 diazomethane 
• 67857-97-0 4-(2-nitrophenyl)-n-butyric acid 
• 1821-12-1 4-Phenylbutyric acid 
• 75-36-5 acetyl chloride 

Downstream Products

• 20637-09-6 methyl 4-(4-aminophenyl)butanoate 
• 1146975-30-5 2-(3-(4-Nitrophenyl)propyl)-4,5-dihydro-1H-imidazole 
• 96912-02-6 4-(4-nitrophenyl)butyraldehyde 
• 1450984-23-2 C₂₂H₃₃NO₄ 
• 1146975-11-2 4-(4-((2-cyanopropan-2-yl)amino)phenyl)butanenitrile 
• 71825-33-7 4-[(4-amino)phenyl]butyrylnitrile 
• 22978-64-9 4-(4-nitro-phenyl)-butyronitrile 
• 1192366-93-0 N-(3-(3,4-dichlorophenylamino)propyl)-3-(4-(methylsulfonamido)phenyl)propanamide 
• 1192366-89-4 N-(3,4-dichlorophenethyl)-4-(4-(methylsulfonamido)-phenyl)butanamide 
• 1192366-08-7 methyl 4-(4-(methylsulfonamido)phenyl)butanoate 
• 55774-31-7 4-{4-[bis-(2-chloro-propyl)-amino]-phenyl}-butyric acid 
• 305-03-3 chlorambucil 
• 130031-42-4 Acridin-9-yl-(3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propyl)-amine 
• 130198-76-4 methyl 3-<4-phenyl>butyrate 

Relevant articles and documents

Mass spectrometry of chlorambucil, its degradation products, and its metabolite in biological samples

A sensitive and specific method for the determination of chlorambucil and its metabolite in biological fluids is reported. The method is based on selected-ion monitoring detection following simple extraction of the parent compound, its metabolite, and an internal standard (chlorambucil-d8) from plasma and urine samples. The precision (reproducibility) of the method was 94.3 ± 1.3% with 200 ng of chlorambucil added to 1 ml of plasma. Chlorambucil degradation or alkylation of plasma proteins was minimal with plasma incubated at 24° for 4 hr. However, chlorambucil recovery decreased to 56% after plasma incubation at 37° for 4 hr. Three chlorambucil degradation products in ethyl acetate solution were found, and their structures were studied by mass spectrometry.

Histone deacetylase inhibitors

This invention relates to novel Histone deacetylases inhibitors. Also disclosed is a method for treating mucositis or cancer with these inhibitors.

CARBOXYLIC DERIVATIVES FOR USE IN THE TREATMENT OF CANCER

The invention provides novel compounds of formula (I), wherein: R1 is a radical derived from one of the known ring systems; R2 is a phenyl radical optionally substituted; Xn represents a birradical selected from the group consisting of: -(CH2)1-4-, (C2-C4)-alkenyl, (C2-C4)alkynyl, -S-(CH2)1-3-#, and -(CH2)1-3-O-#; wherein the symbol # indicates the position at which Xn is attached to R1; Yn is a birradical selected from the group consisting of: -(CH2)2-4-, -S-(CH2)1-3#, and -O-(CH2)1-3-#,; where in the symbol # indicates the position at which Yn is attached to R2; and R3 is a radical selected from the group consisting of: -OR4. The compounds of formula (I) are useful in the treatment of cancer

Synthesis, structural activity-relationships, and biological evaluation of novel amide-based allosteric binding site antagonists in NR1A/NR2B N-methyl-d-aspartate receptors

The synthesis and structure-activity relationship analysis of a novel class of amide-based biaryl NR2B-selective NMDA receptor antagonists are presented. Some of the studied compounds are potent, selective, non-competitive, and voltage-independent antagonists of NR2B-containing NMDA receptors. Like the founding member of this class of antagonists (ifenprodil), several interesting compounds of the series bind to the amino terminal domain of the NR2B subunit to inhibit function. Analogue potency is modulated by linker length, flexibility, and hydrogen bonding opportunities. However, unlike previously described classes of NR2B-selective NMDA antagonists that exhibit off-target activity at a variety of monoamine receptors, the compounds described herein show much diminished effects against the hERG channel and α1-adrenergic receptors. Selections of the compounds discussed have acceptable half-lives in vivo and are predicted to permeate the blood-brain barrier. These data together suggest that masking charged atoms on the linker region of NR2B-selective antagonists can decrease undesirable side effects while still maintaining on-target potency.

A new robust and versatile tetradentate linker for amides to be cleaved under mild conditions by unusual complexation of the amide nitrogen to Cu ++

The concept of weakening amide bonds by the rather unusual forced complexation of nitrogen to Cu++ is not limited to tridentate ligands and was extended in this work to tetradentate ligands as well. The use of cyclic tetradentate ligands was to no avail, but an open-chain and more-flexible tetradentate ligand allowed mild cleavage by methanolysis after complexation. The principle was applied to the development of a new linker for solid-phase chemistry, which was proven to be extremely robust, yet allowed mild cleavage after activation by Cu ++ complexation. Its stability and versatility was demonstrated by the successful application to a whole plethora of different types of reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

Separation tagging with cyclodextrin-binding groups: Mitsunobu reactions with bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD) and bis-(1-adamantylmethyl) azodicarboxylate (BadMAD)

A new method for separation tagging with cyclodextrin-binding groups is introduced and is exemplified in the context of the Mitsunobu reaction with adamantyl tags. HPLC experiments showed that molecules containing adamantyl groups were especially well retained on Sumichiral OA7500 β-methylated cyclodextrin bonded silica columns relative to many other types of molecules. Two new Mitsunobu reagents, bis-(1-adamantylmethyl) azodicarboxylate (BadMAD) and bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD), were prepared, used in typical Mitsunobu reactions and separated with both β-methylated cyclodextrin bonded silica and standard silica.

Fluorous Mitsunobu reagents and reactions

A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H 4)2PPh] and new [C8F17CH2CH2C6H 4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)N=NCOOCH 2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction (spe) over fluorous silica provides clean products in excellent yields. The fluorous fraction containing the oxidized phosphine oxide and the reduced hydrazide can be readily separated and the starting reagents can be regenerated by appropriate redox reactions in high yield for reuse.

Unexpected Selectivity in the Alkylation of Polyazamacrocycles

Reaction of equivalent amounts of free base polyazamacrocycles with an alkyl halide in a nonpolar, aprotic solvent affords the mono-N-alkylation product as its monohydrohalide salt in high yield with excellent selectivity.This unexpected selectivity has been explained in terms of the high affinity of the alkylated product for a single proton which attenuates the nucleophilicity of the remaining nitrogen atoms.Selectivity is dependent upon a number of factors including macrocycle ring size, solvent polarity, and the steric nature of the electrophile.The approach has been allowed for a short, convergent route to bifunctional lanthanide chelators which are useful in therapeutic applications.

Quinazoline derivatives possessing anti-tumor activity

The invention relates to quinazoline derivatives, or pharmaceutically-acceptable salts thereof, which possess anti-tumor activity; to processes for their manufacture; and to pharmaceutical compositions containing them. The invention provides a quinazoline of the formula: STR1 wherein R1 is hydrogen or amino, or alkyl or alkoxy each of up to 6 carbon atoms; or R1 is substituted alkyl or alkoxy each of up to 3 carbon atoms; R2 is hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, halogenoalkyl or cyanoalkyl each of up to 6 carbon atoms; Ar is phenylene or heterocyclene; L is a group of the formula --CO.NH--, --NH.CO--, --CO.NR3 --, --NR3. CO--, --CH=CH--, --CH2 O--, --OCH2, --CH2 S--, --SCH2 --, --CO.CH2 --, --CH2.CO-- or --CO.O--, wherein R3 is alkyl of up to 6 carbon atoms; and Y is aryl or heteroaryl or a hydrogenated derivative thereof: or Y is a group of the formula --A--Y1 in which A is alkylene, cycloalkylene, alkenylene or alkynylene each of up to 6 carbon atoms and Y1 is aryl or heteroaryl or a hydrogenated derivative thereof; or a pharmaceutically-acceptable salt thereof.

1-Aryl-3-(2-chloroethyl) ureas: Synthesis and in vitro assay as potential anticancer agents

1-Aryl-3-(2-chlorethyl) ureas and 1-aryl-3-nitrose-3-(2-chloroethyl) ureas, derived from 4-phenylbutyric acid and alkylanillines, were synthesized and their cytotoxicity was evaluated on human adenocarcinoma cells in vitro. Methyl 4-[p-[3-(2-chloroethyl)ureido]-phenyl]butyrate, 4-methyl [3-(2-chloroethyl)ureido]benzene, and 4-butyl[3-(2-chloroethyl)ureido]benzene were found to be at least as cytotoxic as 4-[p-[bis-(2-chloroethyl)amino]phenyl]butyric acid (chlorambucil), while their N-nitrose derivatives were inactive.