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2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE is a chemical compound with the molecular formula C10H12BrNO2. It is a derivative of acetamide and contains a bromine atom, a methoxy group, and a methyl group, as well as a phenyl ring. 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE is often used in organic synthesis and pharmaceutical research, and it may have potential applications in the development of new drugs and medical treatments. Its specific properties and potential uses may vary depending on the context and the specific research or development goals.

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  • 144581-86-2 Structure
  • Basic information

    1. Product Name: 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE
    2. Synonyms: 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE
    3. CAS NO:144581-86-2
    4. Molecular Formula: C10H12BrNO2
    5. Molecular Weight: 258.11178
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 144581-86-2.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE(CAS DataBase Reference)
    10. NIST Chemistry Reference: 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE(144581-86-2)
    11. EPA Substance Registry System: 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE(144581-86-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 144581-86-2(Hazardous Substances Data)

144581-86-2 Usage

Uses

Used in Organic Synthesis:
2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE is used as an intermediate in organic synthesis for the production of various chemical compounds. Its unique structure, which includes a bromine atom, a methoxy group, and a methyl group, allows it to be a versatile building block in the synthesis of a wide range of organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE is used as a research compound for the development of new drugs and medical treatments. Its specific properties and potential uses may vary depending on the context and the specific research or development goals. 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE's unique structure and functional groups make it a promising candidate for the design and synthesis of novel pharmaceutical agents.
Used in Drug Development:
2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE may have potential applications in the development of new drugs and medical treatments. Its unique structure and functional groups can be utilized to design and synthesize novel pharmaceutical agents with specific therapeutic properties. 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE's potential uses in drug development may include the treatment of various diseases and conditions, depending on the specific research or development goals.

Check Digit Verification of cas no

The CAS Registry Mumber 144581-86-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,4,5,8 and 1 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 144581-86:
(8*1)+(7*4)+(6*4)+(5*5)+(4*8)+(3*1)+(2*8)+(1*6)=142
142 % 10 = 2
So 144581-86-2 is a valid CAS Registry Number.

144581-86-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE

1.2 Other means of identification

Product number -
Other names N-(4-methoxyphenyl)benzimidoyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:144581-86-2 SDS

144581-86-2Relevant articles and documents

Synthesis of Peptoid-Based Class I-Selective Histone Deacetylase Inhibitors with Chemosensitizing Properties

Krieger, Viktoria,Hamacher, Alexandra,Cao, Fangyuan,Stenzel, Katharina,Gertzen, Christoph G. W.,Sch?ker-Hübner, Linda,Kurz, Thomas,Gohlke, Holger,Dekker, Frank J.,Kassack, Matthias U.,Hansen, Finn K.

, p. 11260 - 11279 (2019)

There is increasing evidence that histone deacetylase (HDAC) inhibitors can (re)sensitize cancer cells for chemotherapeutics via "epigenetic priming". In this work, we describe the synthesis of a series of class I-selective HDAC inhibitors with 2-aminoanilides as zinc-binding groups. Several of the synthesized compounds revealed potent inhibition of the class I HDAC isoforms HDAC1, HDAC2, and/or HDAC3 and promising antiproliferative effects in the human ovarian cancer cell line A2780 and the human squamous carcinoma cell line Cal27. Selected compounds were investigated in a cellular model of platinum resistance. In particular, compound 2a revealed potent chemosensitizing properties and full reversal of cisplatin resistance in Cal27CisR cells. This effect is related to a synergistic increase in caspase 3/7 activation and induction of apoptosis. Thus, this work demonstrates that pan-HDAC inhibition or dual class I/class IIb inhibition is not required for full reversal of cisplatin resistance.

Access to imidazo[1,2-a]imidazolin-2-ones and functionalization through Suzuki-Miyaura cross-coupling reactions

Grosse, Sandrine,Pillard, Christelle,Himbert, Franck,Massip, Stephane,Leger, Jean Michel,Jarry, Christian,Bernard, Philippe,Guillaumet, Gerald

, p. 4146 - 4155 (2013)

We report herein a synthetic pathway to new 6(5)-bromo-5(6)- methylimidazo[1,2-a]imidazolin-2-ones. The synthetic potential of these scaffolds was demonstrated by displacing bromine by Suzuki-Miyaura cross-coupling reactions. A large panel of boronic acids (aryl, heteroaryl or vinyl) could easily be introduced, giving access to a large and diversified library of 6(5)-substituted 5(6)-methylimidazo[1,2-a]imidazolin-2-ones. A new route to 6(5)-bromo-5(6)-methylimidazo[1,2-a]imidazolin-2-ones have been developed. A novel and effective strategy of functionnalization of these scaffolds throught Suzuki-Miyaura cross coupling reactions is reported. Thanks to this methodology, a large panel of boronic acids were easily introduced, giving access to a diversified library of 6(5)-substituted 5(6)-methylimidazo[1, 2-a]imidazolin-2-ones. Copyright

A new synthetic approach to the imidazo[1,5-: A] imidazole-2-one scaffold and effective functionalization through Suzuki-Miyaura cross coupling reactions

Loubidi,Pillard,El Hakmaoui,Bernard,Akssira,Guillaumet

, p. 7229 - 7238 (2016)

We report herein a synthetic pathway to new 7-bromo-1-(4-methoxybenzyl)-5-methyl-imidazo[1,5-a]imidazole-2-one. The synthetic potential of this scaffold was demonstrated by displacing bromine by Suzuki-Miyaura cross-coupling reactions. A large panel of bo

BENZYLAMIDE DERIVATIVES AS INHIBITORS OF TRANSFORMING GROWTH FACTOR-BETA RECEPTOR I/ALK5

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Page/Page column 33, (2021/06/04)

The present invention relates to novel benzylamide derivatives of formula (I) to processes for the preparation of said compounds; to pharmaceutical compositions comprising said compounds and to said compounds for use in the treatment of pathological conditions or diseases that can improve by inhibition of transforming growth factor-β receptor I (TGFβRI)/ALK5, such as diseases and disorders associated to fibrotic conditions of gastrointestinal system, skin and eyes, to methods for the treatment and/or prevention of said diseases or pathological conditions and to combinations comprising said compounds and further comprising therapeutically effective amounts of other therapeutic agents useful for the treatment of said diseases or pathological conditions.

Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity

Nimbarte, Vijaykumar D.,Wirmer-Bartoschek, Julia,Gande, Santosh L.,Alshamleh, Islam,Seibert, Marcel,Nasiri, Hamid Reza,Schnütgen, Frank,Serve, Hubert,Schwalbe, Harald

supporting information, p. 1667 - 1679 (2021/03/24)

Lead-optimization strategies for compounds targeting c-Myc G-quadruplex (G4) DNA are being pursued to develop anticancer drugs. Here, we investigate the structure-activity- relationship (SAR) of a newly synthesized series of molecules based on the pyrrolidine-substituted 5-nitro indole scaffold to target G4 DNA. Our synthesized series allows modulation of flexible elements with a structurally preserved scaffold. Biological and biophysical analyses illustrate that substituted 5-nitroindole scaffolds bind to the c-Myc promoter G-quadruplex. These compounds downregulate c-Myc expression and induce cell-cycle arrest in the sub-G1/G1 phase in cancer cells. They further increase the concentration of intracellular reactive oxygen species. NMR spectra show that three of the newly synthesized compounds interact with the terminal G-quartets (5′- and 3′-ends) in a 2 : 1 stoichiometry.

Design, synthesis and biological evaluation of novel Pseudomonas aeruginosa DNA gyrase B inhibitors

Balraju, Vadla,Jogula, Sridhar,Krishna, Vagolu Siva,Meda, Nikhila,Sriram, Dharmarajan

, (2020/05/08)

In the present study, we attempted to develop a novel class of compounds active against Pseudomonas aeruginosa (Pa) by exploring the pharmaceutically well exploited enzyme targets. Since, lack of Pa gyrase B crystal structures, Thermus thermophilus gyrase B in complex with novobiocin (1KIJ) was used as template to generate model structure by performing homology modeling. Further the best model was validated and used for high-throughput virtual screening, docking and dynamics simulations using the in-house database for identification of Pa DNA gyrase B inhibitors. This study led to an identification of three lead molecules with IC50 values in range of 6.25–15.6 μM against Pa gyrase supercoiling assay. Lead-1 optimization and expansion resulted in 15 compounds. Among the synthesized compounds six compounds were shown good enzyme inhibition than Lead-1 (IC50 6.25 μM). Compound 13 emerged as the most potential compound exhibiting inhibition of Pa gyrase supercoiling with an IC50 of 2.2 μM; and in-vitro Pa activity with MIC of 8 μg/mL in presence of efflux pump inhibitor; hence could be further developed as novel inhibitor for Pa gyrase B.

First Nondiscriminating Translocator Protein Ligands Produced from a Carbazole Scaffold

Cheng, Hei Wun Alison,Sokias, Renee,Werry, Eryn L.,Ittner, Lars M.,Reekie, Tristan A.,Du, Jonathan,Gao, Quanqing,Hibbs, David E.,Kassiou, Michael

supporting information, p. 8235 - 8248 (2019/10/11)

Development of neuroinflammation agents targeting the translocator protein (TSPO) has been hindered by a common single nucleotide polymorphism (A147T) at which TSPO ligands commonly lose affinity. To this end, carbazole acetamide scaffolds were synthesized and structure activity relationships elaborated to explore the requirements for high-affinity binding to both TSPO wild type (WT) and the polymorphic TSPO A147T. This study reports high binding affinity and nondiscriminating TSPO ligands.

Design, synthesis, fungicidal activity and molecular docking studies of novel 2-((2-hydroxyphenyl)methylamino)acetamide derivatives

Tang, Zilong,Li, Xinxing,Yao, Yuan,Qi, Yongcun,Wang, Ming,Dai, Ningning,Wen, Yuhao,Wan, Yichao,Peng, Lifen

, p. 2572 - 2578 (2019/03/26)

A series of novel 2-hydroxyphenyl substituted aminoacetamides was designed by molecular hybridization of the aminoacetamide scaffold and 2-hydroxyphenyl motif. The target compounds were synthesized and their fungicidal activities were evaluated. Some of the target compounds showed excellent antifungal activities against S. sclerotiorum and P. capsici. Significantly, compounds 5e displayed the most potent activity against S. sclerotiorum with EC50 = 2.89 μg/mL, which was lower than that of commercial chlorothalonil. The systematic studies provided strong confidence that the hydroxyl group and the carbonyl group are crucial for the fungicidal activity. Molecular docking studies suggest that SDH enzyme could be one of the potential action targets of our compounds.

METHODS AND COMPOSITIONS FOR SELECTIVE AND TARGETED CANCER THERAPY

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Page/Page column 256, (2015/03/28)

Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.

PARP INHIBITORS

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Page/Page column 43; 44, (2013/03/28)

The present application disclosed compounds of Formula I wherein variables R1 and R2 are defined as described herein, which are inhibitors of PARP and provides compounds and compositions containing the compounds of Formula I. The pre

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