7242-16-2

Usage

InChI:InChI=1/C10H8ClNO3/c11-7-1-3-8(4-2-7)12-9(13)5-6-10(14)15/h1-6H,(H,12,13)(H,14,15)/b6-5-

Upstream product

• 108-31-6 maleic anhydride 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 1631-29-4 N-(4-chlorophenyl)maleimide 
• 850148-32-2 3-chloro-1-(4-chlorophenyl)succinimide 
• 19990-27-3 5-(4-chlorophenylimino)-5H-furan-2-one 
• 72889-95-3 (Z)-3-(4-Chloro-phenylcarbamoyl)-acrylic acid methyl ester 
• 105450-99-5 Cr(COOCHCHCONHC₆H₄Cl)3 
• 105367-01-9 [Ni(O₂CCHCHC(O)NH(C₆H₄)Cl)2(H₂O)2] 
• 86396-55-6 4-<4-Chlor-anilino>-4-oxo-buttersaeure-methylester 
• 17722-53-1 3-(4-Chlor-phenylcarbamoyl)-propionsaeure-aethylester 
• 544476-12-2 C₁₂H₁₂ClNO₃ 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel benzylidene-succinimide derivatives as noncytotoxic antiangiogenic inhibitors with anticolorectal cancer activity in vivo

A novel series of benzylidene-succinimide derivatives were synthesized, characterized and evaluated for their cytotoxicities against HCT116, and SW480 cancer cells and NCM460 normal human cells. Their antiangiogenic capabilities were evaluated using a chick chorioallantoic membrane (CAM) assay. The compound, XCF-37b, was selected as the most potent antiangiogenic inhibitor with noncytotoxicity to evaluate the pharmacological effects on human umbilical vein endothelial cells (HUVECs) and cancer cells in vivo and in vitro. The results showed that XCF-37b inhibited HT29-cell colon tumor growth in vivo, without showing cytotoxicity against the five other cancer cell lines in vitro. Experiments confirmed that XCF-37b had obvious antiangiogenic activity by HUVEC migration and invasion and rat aortic ring angiogenesis ex vivo. Mechanism studies showed that XCF-37b inhibited the AKT/mTOR and VEGFR2 signaling pathways, as evidenced by decreased expressions of phosphor-AKT (p-AKT), p-mTOR, p-VEGFR2 (Tyr175), p-Src (Tyr416), p-FAK (Tyr925), and p-Erk1/2 (Thr202/Tyr204). Moreover, XCF-37b significantly decreased the protein expressions of matrix metalloproteinase-2 (MMP-2), MMP-9 and hypoxia-inducible factor-1α (HIF-1α). XCF-37b generally regulated angiogenic inhibition through several regulatory pathways, without significantly interfering with colorectal cancer cell growth.

Improvement of thermal properties of poly(vinyl chloride) using chemical blending assisted ultrasonic technique

The thermal stabilization of poly(vinyl chloride) through blending techniques has been studied. Poly(vinyl chloride) was blended with modified polymer (cellulose acetate-diallyl amine) in different compositions to improve the thermal stability of poly(vinyl chloride). The thermal stability and morphology of the blend films were characterized by scanning electron microscope (SEM) and thermogravimetry. The results revealed that the presence of modified cellulose acetate improved the thermal stability of poly(vinyl chloride). This was attributed to the thermal stable diallylamine moieties among the cellulose acetate chains. The addition of traces of maleimide derivatives to poly(vinyl chloride) prior to the blend process led to an extra thermal stability of the blend film as shown from the values of the initial decomposition temperature (To) measured by thermogravimetry.

Triethylamine-catalyzed synthesis of oxazepine from maleamic acids

2-Thioxo-1,3-oxazepine-4,7-dione compounds were obtained via triethylamine-catalyzed condensation of maleamic acids with thiophosgene under anhydrous conditions. This method features relatively a simple methodology, use of inexpensive reagents, convenient operating conditions and high yields.

1,3-dipolar cycloaddition reactions leading to the synthesis of new 2,3,5-triaryl-4h,2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-diones

Cycloaddition of C,N-diphenylnitrones 1 to N-aryl maleimides 2 afforded two diastereomeric isoxazolidines with high selectivity. The structure and steric configuration of the adducts have been assigned on the basis of 1H NMR, 1H NMR COSY, 13C NMR and IR spectroscopy. The π-π stacking interactions between maleimide's and nitrone's aromatic rings during the 1,3-dipolar cycloaddition were assumed to control the exo-endo selectivity of the reaction. Thus, the exo-endo ratio depends upon the position of the substituent present on the C-phenyl ring of the C,N-diphenylnitrones.

One-pot regioselective synthesis of novel 1-N-methyl-spiro[2,3']oxindole-spiro[3,3"]-1"-N-arylpyrrolidine-2",5"-dione-4-arylpyrrolidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylide

An atom economic and facile synthesis of novel dispiro-oxindole-pyrrolidines has been achieved via a three-component tandem cycloaddition of azomethine ylide generated in situ from isatin and sarcosine by decarboxylative condensation with N-aryl-3-benzylidene-pyrrolidine-2,5-dione derivatives as dipolarophiles. The salient features of synthetic procedure are characterized by the mild reaction conditions, high yields, high regioselectivity and stereoselectivity, one-pot procedure, and operational simplicity. This regioselectivity was assumed to be under the influence of π-π stacking interactions between the aromatic rings of azomethine ylide and N-aryl-3-benzylidene-pyrrolidine-2,5-diones that further control the exo-endo selectivity of the reaction 1,3-dipolar cycloaddition. The regiochemistry and structures of the cycloadducts were determined with spectroscopic data.

DABCO-catalyzed [3+2] cycloaddition reactions of azomethine imines with N-aryl maleimides: Facile access to dinitrogen-fused heterocycles

DABCO-catalyzed [3+2] cycloaddition of azomethine imines with maleimides has been developed. This method could efficiently furnish dinitrogen-fused tetracyclic heterocycles in high levels of regioselectivity and with good yields.

An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters

Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOCl2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC. HCl and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOCl 2 at 0-5°C give the monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group of the ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.

Solvent free preparation of n-substituted maleanilic acid

Six N-maleanilic acids namely N-(4-carboxy)maleanilic acid (CAMAA), N-(4- bromo)maleanilic acid (BMAA), N-(4-hydroxy)maleanilic acid (HMAA), N-(3-hydroxy)maleanilic acid (mHMAA), N-(4-chloro)maleanilic acid (CMAA) and N-(4-methyl)maleanilic acid (MMAA) we

A facile and green synthesis of N-substituted imides

Anhydrides 1, 6 and 10 have been reacted, independently, with aromatic primary amines 2 in solid phase by simple physical grinding of reactants with p-toluenesulphonicacid as a catalyst to yield corresponding open chain derivatives, monoacid monoamides3,7 and 11 respectively. The latter have each been transformed into the corresponding cyclic derivatives, i.e. imides 5, 9 and 13 respectively in solid phase by simple physical grinding of each with K 2CO3, alkylating agent and tetrabutylammoniumbromide as a catalyst with short reaction times. These cyclic imides can also be obtained by physical grinding of each of 3, 7 and 11 with dicyclohexylcarbodimide as a dehydrating agent in solid phase.

Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides

Itaconic anhydride reacts with aryl amines to give a substituent controlled equilibrium mixture of regioisomeric (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4- (arylamino)but-2-enoic acids. Electron-donating groups favor nucleophilic attack on C-5 carbonyl, while the presence of electron-withdrawing groups enhances the bias for attack on C-2 carbonyl. The treatment of (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids with SOCl2-Et 3N in THF provided the corresponding maleimides in high yields while under the same conditions the maleic anhydride aryl amine addition products gave predominately the corresponding 3-chloro-1-arylpyrrolidine-2,5-diones and maleimides in substituent dependent ratio. TUeBITAK, 2012.