15386-80-8

Usage

Uses

Used in Chemical Industry:
2-Cyano-N-(3,4-dichlorophenyl)acetamide is used as a research and development compound for [application reason] in the chemical industry. The specific application reason is not provided in the materials, but it is likely used for the synthesis of other compounds or as an intermediate in chemical processes.
Since the provided materials do not mention any other specific applications or industries for 2-Cyano-N-(3,4-dichlorophenyl)acetamide, the above usage is the only one that can be listed based on the available information. Further research and evaluation would be necessary to identify additional uses or industries where 2-CYANO-N-(3,4-DICHLOROPHENYL)ACETAMIDE might be applied.

InChI:InChI=1/C9H6Cl2N2O/c10-7-2-1-6(5-8(7)11)13-9(14)3-4-12/h1-2,5H,3H2,(H,13,14)

Upstream product

• 372-09-8 cyanoacetic acid 
• 95-76-1 m,p-dichloroaniline 
• 105-56-6 ethyl 2-cyanoacetate 
• 36140-83-7 1-cyanoacetyl-3,5-dimethylpyrazole 

Downstream Products

• 136186-44-2 (Z)-3-(4-Chloro-phenyl)-2-cyano-N-(3,4-dichloro-phenyl)-3-hydroxy-acrylamide 
• 62004-04-0 (2Z)-N-(3,4-dichlorophenyl)-2-cyano-3-hydroxybut-2-enamide 
• 63927-53-7 2-cyano-3-ethoxy-but-2-enoic acid (3,4-dichloro-phenyl)-amide 
• 68808-66-2 1-(cyano-3',4'-dichlorophenylcarbamoylmethylene)-3-imino-isoindoline 
• 1127247-86-2 C₉H₅Cl₂N₃O₂ 

Relevant academic research and scientific papers

Identification of Novel Fused Heteroaromatics-Based MALT1 Inhibitors by High-Throughput Screening to Treat B Cell Lymphoma

Development of mucosa-associated lymphoid tissue lymphoma translocation protein 1 (MALT1) inhibitors is of great value and significance in the treatment of neoplastic disorders and inflammatory and autoimmune diseases. However, there is a lack of effective MALT1 inhibitors in clinic. Herein, a novel class of potent 5-oxo-1-thioxo-4,5-dihydro-1H-thiazolo[3,4-a]quinazoline-based MALT1 inhibitors and their covalent derivatives were first identified and designed through high-throughput screening. We demonstrated that compounds 15c, 15e, and 20c effectively inhibited the MALT1 protease and displayed selective cytotoxicity to activated B cell-like diffuse large B cell lymphoma with low single-digit micromolar potency. Furthermore, compound 20c specifically repressed NF-κB signaling and induced cell apoptosis in MALT1-dependent TMD8 cells in a dose-dependent manner. More importantly, 20c showed good pharmacokinetic properties and antitumor efficacy with no significant toxicity in the TMD8 xenograft tumor model. Collectively, this study provides valuable lead compounds of MALT1 inhibitors for further structural optimization and antitumor mechanism study.

Development of Novel AKR1C3 Inhibitors as New Potential Treatment for Castration-Resistant Prostate Cancer

Aldo-keto reductase (AKR) 1C3 catalyzes the synthesis of active androgens that promote the progression of prostate cancer. AKR1C3 also contributes to androgen-independent cell proliferation and survival through the metabolism of prostaglandins and reactive aldehydes. Because of its elevation in castration-resistant prostate cancer (CRPC) tissues, AKR1C3 is a promising therapeutic target for CRPC. In this study, we found a novel potent AKR1C3 inhibitor, N-(4-fluorophenyl)-8-hydroxy-2-imino-2H-chromene-3-carboxamide (2d), and synthesized its derivatives with IC50 values of 25-56 nM and >220-fold selectivity over other AKRs (1C1, 1C2, and 1C4). The structural factors for the inhibitory potency were elucidated by crystallographic study of AKR1C3 complexes with 2j and 2l. The inhibitors suppressed proliferation of prostate cancer 22Rv1 and PC3 cells through both androgen-dependent and androgen-independent mechanisms. Additionally, 2j and 2l prevented prostate tumor growth in a xenograft mouse model. Furthermore, the inhibitors significantly augmented apoptotic cell death induced by anti-CRPC drugs (abiraterone or enzalutamide).

2-Imino 2H-chromene and 2-(phenylimino) 2H-chromene 3-aryl carboxamide derivatives as novel cytotoxic agents: synthesis, biological assay, and molecular docking study

The inhibition of AKR1B10 has been recognized as a potential therapeutic approach to the treatment of various types of cancers. A novel series of compounds with imino-2H-chromen and phenylimino-2H-chromen scaffolds were synthesized by Knoevenagel condensation reaction. The in vitro cytotoxic activity of synthesized compounds was evaluated against MOLT-4 and SK-OV-3 cells. Among the tested compounds, N-(3,4-dimethoxyphenyl)-2-(phenylimino)-2H-chromene-3-carboxamide (8g) demonstrated potent inhibitory activity against both examined cell lines. The results of the molecular docking study suggested that this compound is involved in critical hydrogen-bonding interactions with the Val301 and Lue302 of AKR1B10 catalytic site.

3,4-Disubstituted isothiazoles: Novel potent inhibitors of VEGF receptors 1 and 2

Novel derivatives of isothiazoles are described as potent ATP-competitive inhibitors of vascular endothelial growth factor receptors I and II (VEGFR-1/2). A number of compounds exhibited VEGFR-2 inhibitory activity comparable to that of Vatalanib in both HTRF enzymatic and cellular assays. Several derivatives featuring bulky meta-substituents in the amide portion of the molecule displayed 4- to 8-fold specificity for VEGFR-2 versus VEGFR-1. Active molecules also showed high intrinsic permeability (>30 × 10-5 cm/min) across Caco-2 cell monolayer.

ortho-Substituted azoles as selective and dual inhibitors of VEGF receptors 1 and 2

We have developed a series of novel potent ortho-substituted azole derivatives active against kinases VEGFR-1 and VEGFR-2. Both specific and dual ATP-competitive inhibitors of VEGFR-2 were identified. Kinase activity and selectivity could be controlled by varying the arylamido substituents at the azole ring. The most specific molecule (17) displayed >10-fold selectivity for VEGFR-2 over VEGFR-1. Compound activities in enzymatic and cell-based assays were in the range of activities for reported clinical and development candidates (IC50 30 × 10-5 cm/min) is indicative of their potential for intestinal absorption upon oral administration.

Structural influence on the intermolecular/intramolecular hydrogen bonding in solid state of substituted leflunomides: Evidence by X-ray crystal structure

We report the results of an X-ray crystal structure study of nine substituted leflunomide metabolite analogs (LFM). Comparison of the hydrogen bonding characteristics exhibited by these structurally distinct LFM analogs was especially informative about the inter- and intra-molecular hydrogen bonding patterns that exist in the crystal structure of individual compounds. All compounds had the strong intramolecular hydrogen bonds. In addition, with the exception of the 2,5-difluorophenyl substituted LFM analog, all other compounds formed inter- or intra-molecular hydrogen bonds with the halogen atom and the NH group. However, we found that the presence of a fluorine atom at the 2-position on the phenyl ring of the 2,5-difluoro and 2-fluoro derivatives resulted in only one intramolecular hydrogen bond in the structural framework. Conversely, the 3,5-difluoro substituted LFM analog had an intramolecular hydrogen bond common to the other halide substituted derivatives. The anomaly exhibited by the 2,5-difluoro and the 2-fluoro substituted compounds may be owing to the smaller size of fluorine atom in comparison with the chlorine and bromine atoms in the structures of the other analogs. The presence of a fluorine at the 2-position of the phenyl ring may disrupt the intermolecular hydrogen bonding that was observed for the other derivatives due to differences in the crystal packing for these molecules.

Synthesis and Biological Activity of a Series of Diaryl-Substituted α-Cyano-β-hydroxypropenamides, a New Class of Anthelmintic Agents

A series of α-cyano-β-hydroxypropenamides was prepared and tested for anthelmintic activity. α-Cyano-β-hydroxy-N--3-propenamide (1) showed good activity against the nematode Nematospirodes dubius in a mixed parasite infection in mice; several of the analogues were also effective against the cestode Hymenolepis nana.In sheep trials, 1 caused 100percent reduction of the hematophagous nematode Haemonchus contortus after a single dose of 20 mg/kg but did not show satisfactory control of Trichostrongylus colubriformis or Ostertagia circumcincta.Against the liver fluke Fasciola hepatica, 1 suppressed egg production but only temporarily, suggesting that the adult flukes were not eliminated.Mechanism of action studies on 1 using Ascaris mitochondria showed it to be an uncoupler of oxidative phosphorylation.

Phenylamidine derivatives

A compound having the general formula: STR1 wherein Ar is an aryl group (especially an α-naphthyl, β-naphthyl or phenyl group) which may be substituted by one or more C1-4 alkyl, C1-4 alkoxy, methylenedioxy halogen, CF3, NH2 or NO2 groups; A is a --CH2 --, --CHOH--, --CH2 O--, --CH2 S--, --CH2 NH--, --OCH2 --, --SCH2 --, --NH--, --NHCOCH2 --, --CH2 NHCH2 -- or --NHCH2 -- group; Y is O or NH; and B is a single bond and, when A is --CH2 --S, may be a --CH2 --, or --CH(CH3)-- group; and their acid addition salts when Y is NH and their metal salts when Y is O. The compounds and their salts have therapeutic utility in treatment of neuropsychic ailments.