13450-77-6

Basic information

• Product Name: (4-CHLORO-BENZOYLAMINO)-ACETIC ACID
• Synonyms: OTAVA-BB BB7210742318;4-chlorobenzoylglycine;4-chlorohippuricacid;n-(4-chlorobenzoyl)-glycin;n-(4-chlorobenzoyl)glycine;n-(p-chlorobenzoyl)glycine;p-chlorobenzoylglycine;p-chloro-hippuricaci
• CAS NO: 13450-77-6
• Molecular Formula: C₉H₈ClNO₃
• Molecular Weight: 213.62
• Mol File: 13450-77-6.mol

Chemical Properties

• Melting Point: 144-146°
• Boiling Point: 457.2 °C at 760 mmHg
• Flash Point: 230.3 °C
• Appearance: /
• Density: 1.397g/cm³
• Vapor Pressure: 3.74E-09mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Dichloromethane (Slightly, Heated), Methanol (Slightly)
• PKA: 3.43±0.10(Predicted)
• CAS DataBase Reference: (4-CHLORO-BENZOYLAMINO)-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (4-CHLORO-BENZOYLAMINO)-ACETIC ACID(13450-77-6)
• EPA Substance Registry System: (4-CHLORO-BENZOYLAMINO)-ACETIC ACID(13450-77-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 13450-77-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(4-CHLORO-BENZOYLAMINO)-ACETIC ACID is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
In the field of chemical research, (4-CHLORO-BENZOYLAMINO)-ACETIC ACID serves as a valuable compound for studying the effects of structural modifications on the properties and reactivity of molecules. It can be used to explore new reaction mechanisms and develop novel synthetic methods.
Used in Analytical Chemistry:
(4-CHLORO-BENZOYLAMINO)-ACETIC ACID can be employed as a reference material or standard in analytical chemistry for the calibration of instruments and the development of new analytical techniques. Its distinct chemical properties make it suitable for various analytical applications.
Used in Material Science:
The compound may also find applications in material science, where it could be used to develop new materials with specific properties, such as improved stability or reactivity. Its unique structure could contribute to the creation of advanced materials for various industrial applications.

InChI:InChI=1/C9H8ClNO3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5H2,(H,11,14)(H,12,13)/p-1

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 56-40-6 glycine 
• 22887-53-2 2-(4-Chlorphenyl)-4,5-dihydro-1,3-oxazol-5-on 
• 6000-43-7 2-aminoethanoic acid hydrochloride 
• 74-11-3 para-chlorobenzoic acid 
• 59893-99-1 N-(p-chlorobenzoyl)-glycine methyl ester 
• 39735-52-9 N-(4-chloro)benzoyl glycine methyl ester 

Downstream Products

• 353280-77-0 2-(4-chloro-phenyl)-4-ethoxymethylene-4H-oxazol-5-one 
• 40547-10-2 2-(4-chloro-phenyl)-4-(3-nitro-benzylidene)-4H-oxazol-5-one 
• 34108-14-0 4-Benzylidene-2-(4-chlorophenyl)-5-oxo-4,5-dihydro-1,3-oxazole 
• 19500-45-9 3,3'-{4-[2-(4-chloro-phenyl)-5-oxo-oxazol-4-ylidenemethyl]-phenylazanediyl}-bis-propionitrile 
• 40587-92-6 2-(4-chloro-phenyl)-4-(2-nitro-benzylidene)-4H-oxazol-5-one 
• 20063-41-6 3,3'-{4-[2-(4-chloro-phenyl)-5-oxo-oxazol-4-ylidenemethyl]-3-methyl-phenylazanediyl}-bis-propionitrile 
• 75152-15-7 (4-Chloro-benzoylamino)-acetic acid 4-nitro-phenyl ester 
• 102674-43-1 methyl 4-chlorobenzoylglycyl-2-methylalaninate 
• 90448-14-9 2-(4-Chlorophenyl)-4-(4-difluoromethylsulfonylbenzylidene)oxazol-5-one 
• 94670-39-0 4-chloro-N-formylbenzamide 
• 103369-09-1 N-(acetoxymethyl)-4-chloro-benzamide 
• 56-40-6 glycine 
• 74-11-3 para-chlorobenzoic acid 
• 1164485-98-6 2-(4-chlorophenyl)-4-<(E)-1-ethoxyethylidene>-5-oxazolone 

Relevant articles and documents

Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents

As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value of 4Bs was above 526, indicating the favorable safety profile. Interestingly, unlike nucleoside analogue 3TC, 4Bs could significantly inhibit 3.5 kb pgRNA expression. Molecular docking study revealed that 4Bs could fit well into the dimer-dimer interface of HBV core protein by hydrophobic, π–π and H-bond interactions. Considering the potent anti-HBV activity, low toxicity and diverse anti-HBV mechanism from that of nucleoside anti-HBV agent 3TC, compound 4Bs might be a promising lead to develop novel non-nucleoside anti-HBV therapeutic agents, and warranted further investigation.

4-Sulfamoylphenylalkylamides as Inhibitors of Carbonic Anhydrases Expressed in Vibrio cholerae

A current issue of antimicrobial therapy is the resistance to treatment with worldwide consequences. Thus, the identification of innovative targets is an intriguing challenge in the drug and development process aimed at newer antimicrobial agents. The state-of-art of anticholera therapy might comprise the reduction of the expression of cholera toxin, which could be reached through the inhibition of carbonic anhydrases expressed in Vibrio cholerae (VchCAα, VchCAβ, and VchCAγ). Therefore, we focused our interest on the exploitation of sulfonamides as VchCA inhibitors. We planned to design and synthesize new benzenesulfonamides based on our knowledge of the VchCA catalytic site. The synthesized compounds were tested thus collecting useful SAR information. From our investigation, we identified new potent VchCA inhibitors, some of them displayed high affinity toward VchCAγ class, for which few inhibitors are currently reported in literature. The best interesting VchCAγ inhibitor (S)-N-(1-oxo-1-((4-sulfamoylbenzyl)amino)propan-2-yl)furan-2-carboxamide (40) resulted more active and selective inhibitor when compared with acetazolamide (AAZ) as well as previously reported VchCA inhibitors.

Addressing hERG activity while maintaining favorable potency, selectivity and pharmacokinetic properties of PPARδ modulators

One of the most commonly used strategies to reduce hERG (human ether-a-go-go) activity in the drug candidates is introduction of a carboxylic acid group. During the optimization of PPARδ modulators, some of the compounds containing a carboxylic acid were found to inhibit the hERG channel in a patch clamp assay. By modifying the basicity of the imidazole core, potent and selective PPARδ modulators that do not inhibit hERG channel were identified. Some of the modulators have excellent pharmacokinetic profiles in mice.

Design, synthesis, and molecular docking of novel indole scaffold-based VEGFR-2 inhibitors as targeted anticancer agents

A series of new indole derivatives 1–18 was synthesized and tested for their cytotoxic activity on a panel of 60 tumor cell lines. Additionally, molecular docking was carried out to study their binding pattern and binding affinity in the VEGFR-2 active site using sorafenib as a reference VEGFR-2 inhibitor. Based on the molecular docking results, compounds 5a, 5b, 6, 7, 14b, 18b, and 18c were selected to be evaluated for their VEGFR-2 inhibitory activity. Compound 18b exhibited a broad-spectrum antiproliferative activity on 47 cell lines, with GI % ranging from 31 to 82.5%. Moreover, compound 18b was the most potent VEGFR-2 inhibitor with an IC50 value of 0.07 μM, which is more potent than that of sorafenib (0.09 μM). A molecular docking study attributed the promising activity of this series to their hydrophobic interaction with the VEGFR-2 binding site hydrophobic side chains and their hydrogen bonding interaction with the key amino acids Glu885 and/or Asp1046.

PPAR AGONISTS, COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF

Provided herein are compounds and compositions useful in increasing PPARδ activity. The compounds and compositions provided herein are useful for the treatment of PPARδ related diseases (e.g., muscular diseases, vascular disease, demyelinating disease, and metabolic diseases).

Substituted pyrimidine derivatives with Akt inhibiting activity, and preparation method and application thereof

The invention relates to novel substituted pyrimidine derivatives with Akt inhibiting activity and a preparation method thereof, a pharmaceutical composition comprising the substituted pyrimidine derivatives and salts thereof, and application of the substituted pyrimidine derivatives and salts thereof in preparing drugs for preventing and/or treating tumors. The structural formula of the compounds is disclosed as Formula (I) or Formula (II). The compounds have the advantages of novel structure, outstanding Akt inhibiting activity, high safety and low preparation cost, and have favorable application prospects in preparing antineoplastic drugs.

Synthesis of 4-(thiazol-2-ylamino)-benzenesulfonamides with carbonic anhydrase I, II and IX inhibitory activity and cytotoxic effects against breast cancer cell lines

A series of 4-(thiazol-2-ylamino)-benzenesulfonamides was synthesized and screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibitory and cytotoxic activity on human breast cancer cell line MCF-7. Human (h) CA isoforms I, II and IX were included in the study. The new sulfonamides showed excellent inhibition of all three isoforms, with KIs in the range of 0.84-702 nM against hCA I, of 0.41-288 nM against hCA II and of 5.6-29.2 against the tumor-associated hCA IX, a validated anti-tumor target, with a sulfonamide (SLC-0111) in Phase I clinical trials for the treatment of hypoxic, metastatic solid tumors overexpressing CA IX. The new compounds showed micromolar inhibition of growth efficacy against breast cancer MCF-7 cell lines.

Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives

Four series of sulfonamides incorporating chromone moieties were synthesized and assessed for their cytotoxic activity against MCF-7 and A-549 cell lines, considering the fact that some of these tumors overexpress isoforms of carbonic anhydrase (CA, EC 4.2.1.1) which is inhibited by sulfonamides. Most new sulfonamides showed weak inhibitory activity against the offtarget, cytosolic isoforms hCA I, II but effectively inhibited the tumor-associated hCA IX and XII. The most active compounds featured a primary SO2NH2 group and were active in the low micromolar range against MCF-7 and A-549 cell lines. Compound 4a showed IC50 of 0.72 and 0.50 1/4M against MCF-7 and A-549 cell lines, respectively, and was further evaluated for its proapoptotic activity which proved enhanced in both tumor types.

ARYL AND HETEROARYL ETHER COMPOUNDS AS ROR GAMMA MODULATORS

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A convenient method for synthesis of 5-chloro-2-aryloxazole-4-carbaldehyde with vilsmeier reagent

A convenient method for synthesis of 5-chloro-2-aryloxazole-4-carbaldehyde 3 in moderate to good yields had been developed via the Vilsmeier reaction of readily available N-arylglycine 2 at 100 °C, provided a novel route for the construction of nitrogen heterocycles. A series of these compounds were synthesized by this method and optimization of conditions was performed. The Japan Institute of Heterocyclic Chemistry.