68294-03-1

Basic information

• Product Name: 2-(CarboxyMethyl)-4-Methoxybenzoic acid
• Synonyms: 2-(CarboxyMethyl)-4-Methoxybenzoic acid
• CAS NO: 68294-03-1
• Molecular Formula: C₁₀H₁₀O₅
• Molecular Weight: 210.1834
• Mol File: 68294-03-1.mol

Chemical Properties

• Melting Point: 222 °C
• Boiling Point: 409.4±30.0 °C(Predicted)
• Appearance: /
• Density: 1.370±0.06 g/cm3(Predicted)
• PKA: 4.03±0.36(Predicted)
• CAS DataBase Reference: 2-(CarboxyMethyl)-4-Methoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CarboxyMethyl)-4-Methoxybenzoic acid(68294-03-1)
• EPA Substance Registry System: 2-(CarboxyMethyl)-4-Methoxybenzoic acid(68294-03-1)

Safety Data

• Hazardous Substances Data: 68294-03-1(Hazardous Substances Data)

Upstream product

• 3469-07-6 5-methoxy-1H-indene 
• 3469-08-7 6-methoxy-1H-indene 
• 76254-24-5 2-cyanomethyl-4-methoxy-benzoic acid 
• 5111-70-6 5-methoxy-1-indanone 
• 7235-36-1 5-methoxy-indan-1,2-dione 2-oxime 
• 6245-57-4 4-methoxy-2-methylbenzoic acid 
• 616-38-6 carbonic acid dimethyl ester 
• 10516-71-9 3-(3-Methoxy-phenyl)-propionic acid 
• 6099-04-3 3-methoxycinnamic acid 
• 511533-37-2 ethyl β-(5-methoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)-α-oxoacetate 
• 74317-85-4 2-bromo-4-methoxybenzoic acid 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 124-41-4 sodium methylate 
• 91497-75-5 methyl 4-methoxy-2-(2-methoxy-2-oxoethyl)benzoate 
• 444340-29-8 6-benzyloxy-3-methyl-isochromen-1-one 
• 1026419-29-3 6-benzyloxy-3-methylnaphthalen-1-ol 
• 444340-31-2 6-benzyloxy-1-methoxy-3-methylnaphthalene 
• 173465-33-3 <5-Methoxy-2-(N-methyl-N-pent-4-enylaminocarbonyl)phenyl>acetic acid methyl ester 
• 173465-34-4 2-<5-Methoxy-2-(N-methyl-N-pent-4-enylaminocarbonyl)phenyl>-2-diazoacetic acid methyl ester 
• 221133-91-1 4-Methoxy-2-methoxycarbonylmethylbenzoic acid 2-oxo-1,2-dihydropyridin-1-yl ester 
• 918662-40-5 4-acetyl-6-methoxyisochroman-1,3-dione 
• 22117-57-3 3,4-Dihydro-6-methoxy-2-phenylnaphthalene 

Relevant articles and documents

Sulfones as Synthetic Linchpins: Transition-Metal-Free sp3–sp2 and sp2–sp2 Cross-Couplings Between Geminal Bis(sulfones) and Organolithium Compounds

A valuable umpolung strategy that highlights the ambiphilic nature of the bis(phenylsulfonyl)methyl synthon and demonstrates its utility as a synthetic linchpin is reported. Although the bis(phenylsulfonyl)methyl group is typically introduced as an sp3-carbon nucleophile, it is demonstrated that it can also function as an effective sp2-carbon electrophile in the presence of organolithium nucleophiles. Alkyl- and aryllithiums couple with the central carbon of the bis(phenylsulfonyl)methyl unit to ultimately generate trisubstituted alkenes, comprising formal sp3–sp2 and sp2–sp2 cross-couplings between organolithium reagents and bis(sulfones). This process occurs almost instantaneously at ?78 °C in the absence of any transition metals. By developing this curious transformation, it has been demonstrated that bis(phenylsulfonyl)methane is a valuable synthetic linchpin, which can undergo two C?C bond-forming processes as an sp3-nucleophile, followed by a third C?C bond-forming reaction as an effective sp2-electrophile. This discovery significantly enhances the utility of this ubiquitous, but underutilized, linker group.

Synthesis and antitumor activity evaluation of 2-arylisoquinoline-1,3(2H, 4H)-diones in vitro and in vivo

Six 2-(2-acylaminobenzothiazol-6-yl)isoquinoline-1,3(2H,4H)-diones (1a-1f) and five 2-arylisoquinoline-1,3(2H,4H)-diones (1g-1k) were synthesized by refluxing homophthalic anhydrides with 2-acylaminobenzothiazolyl-6-amine or substituted aniline in glacial acetic acid. The cytotoxic activities of 1a-1k were evaluated via MTT method against A431, A549, and PC3. Compound 1b relatively displayed a higher cytotoxic activity than the others. The antitumor effect of 1b were evaluated in established nude mice PANC-1 xenograft model. The results suggest that compound 1b could potentially inhibit tumor growth.

4-(Phenylaminomethylene)isoquinoline-1,3(2H,4H)-diones as potent and selective inhibitors of the cyclin-dependent kinase 4 (CDK4)

The cyclin-dependent kinases (CDKs), as complexes with their respective partners, the cyclins, are critical regulators of cell cycle progression. Because aberrant regulations of CDK4/cyclin D1 lead to uncontrolled cell proliferation, a hallmark of cancer, small-molecule inhibitors of CDK4/cyclin D1 are attractive as prospective antitumor agents. The series of 4-(phenylaminomethylene)isoquinoline-1,3(2H,4H)-dione derivatives reported here represents a novel class of potent inhibitors that selectively inhibit CDK4 over CDK2 and CDK1 activities. In the headpiece of the 4-(phenylaminomethylene) isoquinoline-1,3(2H,4H)-dione, a basic amine substitutent is required on the aniline ring for the CDK4 inhibitory activity. The inhibitory activity is further enhanced when an aryl or heteroaryl substituent is introduced at the C-6 position of the isoquinoline-1,3(2H,4H)-dione core. We present here SAR data and a CDK4 mimic model that explains the binding, potency, and selectivity of our CDK4 selective inhibitors.

1-ARYL-4-SUBSTITUTED ISOQUINOLINES

1-Aryl-4-substituted isoquinolines analogues of Formula (I) and Formula (II) are provided, as follows : wherein R1, R2, R3, R8, R9, A and Ar are defined herein. Such compounds are ligands of C5a receptors. Preferred compounds of Formula (I) and (II) bind to C5a receptors with high affinity and exhibit neutral antagonist or inverse agonist activity at C5a receptors. The present invention also relates to pharmaceutical compositions compositions comprising such compounds, and to the use of such compounds in treating a variety of inflammatory, cardiovascular, and immune system disorders. In addition, the present invention provides labeled 1-aryl-4-substituted isoquinolines, which are useful as probes for the localization of C5a receptors.

Reduced Benzimidazo[2,1-a]isoquinolines. Synthesis and Cytotoxicity Studies

6-Butyl-5,6-dihydrobenzimidazo[2,1-a]isoquinoline, 3,9- and 3,10-dimethoxy, and 3,9- and 3,10-dihydroxy analogues, and their 12-methyl quaternary salts were prepared by a multistep route. Cytotoxicities against 55 human cancer cell lines were measured in the National Cancer Institute screen. The quaternary salts of the dimethoxy compounds (15b/c) were clearly the most active overall, with a mean graph midpoint (MGM) value of 2 μm.