54287-99-9Relevant articles and documents
A short synthesis of 5-methoxy-2,2-dimethyl-2H-1-benzopyran-6-propanoic acid methyl ester
Henry,Jacobs
, p. 5335 - 5338 (2001)
5-Methoxy-2,2-dimethyl-2H-1-benzopyran-6-propanoic acid methyl ester was prepared in five steps and approximately 20% overall yield from 2,4-dihydroxybenzaldehyde. The two key reactions are the chromenylation between the unchelated hydroxyl group and C-3 of the resbenzaldehyde and the demethoxycarbonylation-alkylation of dimethyl malonate with a quaternary ammonium iodide.
Direct preparation method of 5-hydroxy-2, 2-dimethyl-2H-benzofuran-6-formaldehyde
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Paragraph 0025-0029, (2020/10/20)
The invention belongs to the technical field of compound synthesis, and relates to a direct preparation method of 5-hydroxy-2, 2-dimethyl-2H-benzofuran-6-formaldehyde. The preparation method comprisesthe following steps of: (1) dissolving 4-hydroxy-salicylaldehyde, 2-methyl-3-butyne-2-ol and a catalyst in an organic solvent, and carrying out a reflux reaction under the protection of nitrogen until no obvious water is generated; and (2) washing a product obtained after the reaction, collecting an organic phase, and carrying out drying, reduced pressure concentration and column chromatography purification to obtain a faint yellow solid product, namely the 5-hydroxy-2, 2-dimethyl-2H-benzofuran-6-formaldehyde. According to the method, the 2-methyl-3-butyne-2-ol which is low in price and easyto obtain serves as a raw material and reacts with the reaction substrate 4-hydroxy-salicylaldehyde; on the basis of a cascade reaction, the target product is directly obtained through a one-step reaction under the action of the catalyst. The direct preparation method has the advantages of low cost, easy and convenient operation and high production efficiency.
Novel Hypoxia-Inducible Factor 1α (HIF-1α) Inhibitors for Angiogenesis-Related Ocular Diseases: Discovery of a Novel Scaffold via Ring-Truncation Strategy
An, Hongchan,Lee, Seungbeom,Lee, Jung Min,Jo, Dong Hyun,Kim, Joohwan,Jeong, Yoo-Seong,Heo, Mi Jeong,Cho, Chang Sik,Choi, Hoon,Seo, Ji Hae,Hwang, Seyeon,Lim, Jihye,Kim, Taewoo,Jun, Hyoung Oh,Sim, Jaehoon,Lim, Changjin,Hur, Joonseong,Ahn, Jungmin,Kim, Hyun Su,Seo, Seung-Yong,Na, Younghwa,Kim, Seok-Ho,Lee, Jeewoo,Lee, Jeeyeon,Chung, Suk-Jae,Kim, Young-Myeong,Kim, Kyu-Won,Kim, Sang Geon,Kim, Jeong Hun,Suh, Young-Ger
, p. 9266 - 9286 (2018/10/24)
Ocular diseases featuring pathologic neovascularization are the leading cause of blindness, and anti-VEGF agents have been conventionally used to treat these diseases. Recently, regulating factors upstream of VEGF, such as HIF-1α, have emerged as a desirable therapeutic approach because the use of anti-VEGF agents is currently being reconsidered due to the VEGF action as a trophic factor. Here, we report a novel scaffold discovered through the complete structure-activity relationship of ring-truncated deguelin analogs in HIF-1α inhibition. Interestingly, analog 6i possessing a 2-fluorobenzene moiety instead of a dimethoxybenzene moiety exhibited excellent HIF-1α inhibitory activity, with an IC50 value of 100 nM. In particular, the further ring-truncated analog 34f, which showed enhanced HIF-1α inhibitory activity compared to analog 2 previously reported by us, inhibited in vitro angiogenesis and effectively suppressed hypoxia-mediated retinal neovascularization. Importantly, the heteroatom-substituted benzene ring as a key structural feature of analog 34f was identified as a novel scaffold for HIF-1α inhibitors that can be used in lieu of a chromene ring.
Alkyne Carbonyl Metathesis As a Means to Make 4-Acyl Chromenes: Syntheses of (±)-Deguelin and (±)-Munduserone
Nayak, Maloy,Kim, Ikyon
, p. 11460 - 11467 (2015/12/01)
A highly convergent synthetic approach to rotenoid natural products is described. Successful pairing of two building blocks for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready access to 4-acylchromene, a key substruct