A Non-Organometallic Method for the Synthesis of Methyl Ketones from Acyl Chlorides

Hase, Takayuki; SALONEN, K.

doi:10.1080/00397918008064225

Cited by 25 publications

(11 citation statements)

References 9 publications

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“…3-(1-Cyanoethyl)benzoic acid, 12, was converted into acetyl derivative 13 using a stepwise process that involved the conversion of the acid to the corresponding acid chloride followed by treatment with Meldrum's acid in the presence of base and then hydrolytic decarboxylation. 13 Subsequent hydrolysis of nitrile derivative 13 gave substituted hydratropic acid 14, which was treated with thionyl chloride followed by sodium azide in water to generate acyl azide 15 that was used without isolation. Acyl azide 15 was heated to reflux in benzene under a nitrogen atmosphere to generate isocyanate 16.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…All chemical shift values are also reported with multiplicity, coupling constants, and proton count. All 13 C NMR spectra are reported in δ units ppm and are reference to the central line of the triplet at 77.23 ppm if conducted in CDCl 3 or to the central line of the septet at 39.5 ppm for samples in DMSO-d 6 . Coupling constants (J values) are reported in hertz.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Selective and Potent Urea Inhibitors of Cryptosporidium parvum Inosine 5′-Monophosphate Dehydrogenase

Gorla¹,

Mandapati²,

Zhang³

et al. 2012

J. Med. Chem.

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Cryptosporidium parvum and related species are zoonotic intracellular parasites of the intestine. Cryptosporidium is a leading cause of diarrhea in small children around the world. Infection can cause severe pathology in children and immunocompromised patients. This waterborne parasite is resistant to common methods of water treatment and therefore a prominent threat to drinking and recreation water even in countries with strong water safety systems. The drugs currently used to combat these organisms are ineffective. Genomic analysis revealed that the parasite relies solely on inosine-5′-monophosphate dehydrogenase (IMPDH) for the biosynthesis of guanine nucleotides. Herein, we report a selective urea-based inhibitor of C. parvum IMPDH (CpIMPDH) identified by high throughput screening. We performed a SAR study of these inhibitors with some analogues exhibiting high potency (IC50 < 2 nM) against CpIMPDH, excellent selectivity > 1000-fold versus human IMPDH type 2 and good stability in mouse liver microsomes. A subset of inhibitors also displayed potent antiparasitic activity in a Toxoplasma gondii model.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Selective and Potent Urea Inhibitors of Cryptosporidium parvum Inosine 5′-Monophosphate Dehydrogenase

Gorla¹,

Mandapati²,

Zhang³

et al. 2012

J. Med. Chem.

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“…2-(3-Acetylphenyl)propanenitrile (125). The synthesis of 125 was performed according to a previously described procedure . After purification by flash chromatography ( n -hexane/EtOAc 8:2), 125 was obtained pure as a yellow oil (1.19 g, 60% yield).…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis of 125 was performed according to a previously described procedure. 53 After purification by flash chromatography (nhexane/EtOAc 8:2), 125 was obtained pure as a yellow oil (1.19 g, 60% yield). 1 H NMR (CDCl3) δ 7.95 (m, 2H), 7.65 (m, 1H), 7.50 (m, 1H), 4.05 (q, 1H, J ) 7 Hz), 2.70 (s, 3H), 1.75 (d, 3H, J ) 7 Hz).…”

Section: (R)-2-(4-isobutylphenyl)-n-(3-tert-butoxycarbonylaminopropyl...mentioning

confidence: 99%

2-Arylpropionic CXC Chemokine Receptor 1 (CXCR1) Ligands as Novel Noncompetitive CXCL8 Inhibitors

et al. 2005

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The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCL8-induced human PMNs chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.

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“…In another approach to 6, we planned the acylation of key intermediate (3); which would demonstrate the utility of Meldrum's acid (1) in the synthesis of desired ketones. The reaction in fact, represents the stepwise monoalkylation 27 and acylation [34][35][36] of Meldrum's acid. The key intermediate 3 was condensed with 3,3-dimethylacryloyl chloride in dichloromethane and pyridine to give the alkyl acyl Meldrum's acid 7.…”

mentioning

confidence: 99%

Application of Meldrum's Acid in Natural Product Synthesis. Synthesis of Ar-Turmerone and α-Curcumene

Mahulikar

Mane

2006

Journal of Chemical Research

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A Non-Organometallic Method for the Synthesis of Methyl Ketones from Acyl Chlorides

Cited by 25 publications

References 9 publications

Selective and Potent Urea Inhibitors of Cryptosporidium parvum Inosine 5′-Monophosphate Dehydrogenase

Selective and Potent Urea Inhibitors of Cryptosporidium parvum Inosine 5′-Monophosphate Dehydrogenase

2-Arylpropionic CXC Chemokine Receptor 1 (CXCR1) Ligands as Novel Noncompetitive CXCL8 Inhibitors

Application of Meldrum's Acid in Natural Product Synthesis. Synthesis of Ar-Turmerone and α-Curcumene

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