- An improved one-pot cost-effective synthesis of N,N-disubstituted carbamoyl halides and derivatives
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A convenient one-pot procedure is reported for preparing N,N-disubstituted carbamoyl chlorides by using chlorocarbonylsulfenyl chloride as a carbonylating agent. It comprises the reaction of secondary amines with chlorocarbonylsulfenyl chloride in the presence of an aprotic organic solvent to produce the corresponding N,N-disubstituted carbamoyl halides. Insertion of the carbonyl group without using phosgene is the novelty of this method.
- Adeppa,Rupainwar,Misra, Krishna
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- Conversion of Amines to Carbamoyl Chlorides Using Carbon Dioxide as a Phosgene Replacement
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Dialkyl carbamates, generated from amines and carbon dioxide, are converted to their corresponding carbamoyl chlorides using thionyl chloride in the presence of added tertiary amine base.
- McGhee, William D.,Pan, Yi,Talley, John J.
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- "Solvent Friction" and the Entanglement of Long Hydrocarbon Chains
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Rotation about the R2N-COOR bond in carbamates with three alkyl chains (butyl through octadecyl) was investigated by NMR.Even solvents such as hexadecane and mineral oil did not substantially impede the rotation, revealing a surprising absence of "solvent friction" induced by chain entanglement.Possible explanations at the molecular level and the relevance to membrane systems are discussed.
- Menger, F. M.,Mounier, C. E.
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- Synthesis and Biological Evaluation of Celastrol Derivatives with Improved Cytotoxic Selectivity and Antitumor Activities
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Cdc37 associates kinase clients to Hsp90 and promotes the development of cancers. Celastrol, a natural friedelane triterpenoid, can disrupt the Hsp90-Cdc37 interaction to provide antitumor effects. In this study, 31 new celastrol derivatives, 2a - 2d , 3a - 3g , and 4a - 4t , were designed and synthesized, and their Hsp90-Cdc37 disruption activities and antiproliferative activities against cancer cells were evaluated. Among these compounds, 4f , with the highest tumor cell selectivity (15.4-fold), potent Hsp90-Cdc37 disruption activity (IC50= 1.9 μM), and antiproliferative activity against MDA-MB-231 cells (IC50= 0.2 μM), was selected as the lead compound. Further studies demonstrated 4f has strong antitumor activities both in vitro and in vivo through disrupting the Hsp90-Cdc37 interaction and inhibiting angiogenesis. In addition, 4f exhibited less toxicity than celastrol and showed a good pharmacokinetics profile in vivo. These findings suggest that 4f may be a promising candidate for development of new cancer therapies.
- Feng, Jia-Hao,He, Qi-Wei,Hou, Ji-Qin,Hu, Xiao-Long,Long, Huan,Wang, Bao-Lin,Wang, Hao,Wang, Quan,Wang, Rong,Ye, Wen-Cai,Zhang, Li-Xin,Zhang, Xiao-Qi
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p. 1954 - 1966
(2021/07/20)
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- Process for the preparation of phthalic acid dichloride
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Preparation of phthalic acid dichloride (I) comprises reaction of phthalic acid anhydride (II) with phosgene in presence of catalyst (N,N-disubstituted formamide (III)). Preparation of phthalic acid dichloride of formula (I) comprises reaction of phthalic acid anhydride of formula (II) with phosgene in presence of catalyst (N,N-disubstituted formamide (III) of formula (HC(O)-N(R 1>)(R 2>)). R 1>, R 2>1-22C alkyl, 2-22C alkenyl, 3-8C cycloalkyl, 6-10C aryl or 7-12C arylalkyl. Where R 1>, R 2>containing 1-22C alkyl, 2-22C alkenyl amounts to total molecular weight of (III) is at least 269 g/mol. [Image].
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Page/Page column 5; 6
(2008/06/13)
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- Process for the preparation of 1-4-disubstituted-5 (4H)-tetrazolinones
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1,4-Disubstituted-5(4H)-tetrazolinones of the formula (I) STR1 wherein R1, R2 and R3 have the meanings given in the specification), which are known to be useful as herbicides, can be obtained in very good yields by reacting the corresponding 1-substituted-5(4H)-tetrazolinones with the corresponding carbamoyl chlorides in the presence of 4-dimethylaminopyridine.
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- A CONVENIENT PREPARATION OF CERTAIN N,N-DIALKYLCARBAMOYL CHLORIDES
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Certain N,N-dialkylcarbamoyl chlorides (2) were prepared in moderate yields by the reaction of ethyl N,N-dialkylcarbamates (1) with phosphoryl chloride in boiling acetonitrile.
- Hoshino, Osamu,Saito, Keiji,Ishizaki, Miyuki,Umezawa, Bunsuke
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p. 1887 - 1892
(2007/10/02)
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