- Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids
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Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.
- Xu, Xiao-Long,Li, Zhi
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p. 5078 - 5081
(2019/09/03)
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- Synthetic method for drug 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid
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The invention discloses a synthetic method for the drug 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid. The synthetic method comprises the following steps: adding 1,4-dimethoxy-2,5,6-trimethylbenzene and a sodium nitrate solution into a reaction vessel, controlling a stirring speed, carrying out heating, then adding aluminum isopropoxide, and continuing reaction; and carrying outheating, adding a sodium sulfate solution, adding potassium peroxydisulfate in batches within a certain period of time, controlling a stirring speed, adding niobium pentoxide powder, continuing the reaction, carrying out cooling, adding a potassium chloride solution, subjecting the solution to layering to separate an oil layer, washing the oil layer with an ethylene glycol solution, then washing the oil layer with a chloroform solution, carrying out recrystallization in a propargyl alcohol solution, and then carrying out dehydration with dehydrating agent to obtain the finished 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid.
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Paragraph 0013; 0015-0026
(2018/07/30)
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- Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast
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Esterification reactions from cyclic 1,3-diketones and alcohols are carried out in the presence of several Lewis acids. In particular, indium(III) triflate, In(OTf)3, iron(III) triflate, Fe-(OTf)3, copper(II) triflate, Cu(OTf)2, and silver(I) triflate, AgOTf, show high catalytic activities. These reactions proceed through the carbon-carbon bond cleavage by a retro-aldol reaction and were found to be highly regioselective even in the presence of other functional groups. This type of reaction can also be applied to the preparation of the keto esters during the synthesis of seratrodast, which is an antiasthmatic and eicosanoid antagonist.
- Kuninobu, Yoichiro,Kawata, Atsushi,Noborio, Taihei,Yamamoto, Syun-Ichi,Matsuki, Takashi,Takata, Kazumi,Takai, Kazuhiko
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scheme or table
p. 941 - 945
(2010/07/07)
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- Method of treating preeclampsia
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Straight-chain alkanoic acids, substituted at the Ω-carbon atom by a substituted phenyl, naphthyl, furyl, or thienyl group and by a substituted 1,4-benzoquinon-2-yl group are effective in the therapy or prophylaxis of conditions associated with lipid peroxide injury to vascular endothelium particularly preeclampsia and eclampsia in pregnant females.
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- Process for preparing diphenylmethane compounds
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A diphenylmethane compound (III) can be produced in a good yield by allowing a phenol compound (I) to react with a stilbene compound (II) in the presence of methanesulfonic acid STR1
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- Quinone derivatives, their production and use
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Quinone derivatives of the general formula: STR1 (wherein R1 and R2 are the same or different, and independently are a hydrogen atom or a methyl or methoxy group, or R1 and R2 combine with each other to represent --CH=CH--CH=CH--R3 is a hydrogen atom or a methyl group; R4 is an aliphatic, aromatic or heterocyclic group which may be substituted; R5 is a methyl or methoxy group, a hydroxymethyl group which may be substituted or a carboxyl group which may be esterified or amidated; Z is a group represented by --C=C--, --CH=CH--, STR2 n is an integer of 0 to 10; m is an integer of 0 to 3; k is an integer of 0 to 5, provided, however, that in the case of m being 2 or 3, Z and k can vary arbitrarily within the bracketed repeating units) are novel compounds, possess metabolism ameliorating action for polyunsaturated fatty acids, particularly production inhibitory activity of lipid peroxides (antioxidant activity), thromboxane A2 receptor antagonism, or production inhibitory activity of 5-lipoxygenase metabolites in mammals, and of use as drugs, such as antiasthmatic, antiallergic agent and cerebral-circulatory metabolism ameliorating agent.
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- Quinones. 4. Novel eicosanoid antagonists: Synthesis and pharmacological evaluation
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A new series of ω-phenyl-ω-quinonylalkanoic acids and related compounds was synthesized. The compounds were tested for their inhibitory effects on U-44069-induced contraction of the rabbit aorta. (±)-7-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid (4d) (AA-2414) with pA2 value of 8.28 was one of the most potent compounds. Compound 4d inhibited U-46619-induced contraction of the guinea pig lung (pA2 = 8.29) and U-44069-induced aggregation of the guinea pig platelet (IC50 = 3.5 x 10-7 M). Compound 4d displaced the binding of [3H]U-46619 to guinea pig platelets (IC50 = 7.4 x 10-9 M). Compound 4d also showed very potent inhibitory effects with an MED of 0.3 mg/kg (po) on U-46619-, LTD4-, PAF-, or IgG1-induced bronchoconstriction in guinea pigs. The enantiomers of 4d were prepared. The R-(+) isomer 8a was active in both in vitro and in vivo tests, but the S-(-) isomer 8b was much less active. We concluded that the antiasthmatic effects of 4d were based mainly on the TXA2 receptor antagonistic action. In addition, compound 4d showed potent inhibitory effects on PGD2-, PGF(2α)-, and 11-epi-PGF(2α)-induced contraction of the guinea pig tracheal strips. The diverse inhibitory effects might be expressed in terms of eicosanoid-antagonistic activity.
- Shiraishi,Kato,Terao,Ashida,Terashita,Kito
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p. 2214 - 2221
(2007/10/02)
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