- A short synthesis of 5-methoxy-2,2-dimethyl-2H-1-benzopyran-6-propanoic acid methyl ester
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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.
- Henry,Jacobs
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Read Online
- Base-catalyzed condensation of 2-hydroxybenzaldehydes with α,β-unsaturated aldehydes - Scope and limitations
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The base-catalyzed condensation of α,β-unsaturated carbonyl compounds with 2-hydroxybenzaldehydes yielding tetrahydroxanthones and dihydrobenzopyrans has been investigated. A novel access to highly functionalized dihydrobenzopyrans via a mild generation of the dienol of senecialdehyde and subsequent conjugated aldol reaction has been reported.
- Lesch, Bernhard,Toraeng, Jakob,Vanderheiden, Sylvia,Braese, Stefan
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Read Online
- Direct preparation method of 5-hydroxy-2, 2-dimethyl-2H-benzofuran-6-formaldehyde
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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.
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Paragraph 0025-0029
(2020/10/20)
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- Imidazo ring PAR4 antagonist and medical applications thereof
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The invention relates to an imidazo ring compound represented by formula (I) or formula (II), or a pharmaceutically acceptable salt or ester or solvate thereof. The compound disclosed by the inventioncan be used for preparing medicines for preventing or treating thromboembolic diseases.
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Paragraph 0328-0331
(2020/01/12)
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- Novel Hypoxia-Inducible Factor 1α (HIF-1α) Inhibitors for Angiogenesis-Related Ocular Diseases: Discovery of a Novel Scaffold via Ring-Truncation Strategy
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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.
- 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
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p. 9266 - 9286
(2018/10/24)
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- Synthetic method of antitumor deguelin broken-ring structure and amino acid derivatives
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The invention discloses a synthetic method of antitumor deguelin broken-ring structure and amino acid derivative. The antitumor deguelin broken-ring structure and amino acid derivative has a following structural formula, wherein R is side-chain groups of amino acid; the synthetic method includes: 1), condensing 3-methylcrotonaldehyde and 2,4-2-hydroxybenzaldehyde under alkali catalysis condition; 2), methylating a product of step 1) with a methylation reagent under alkali catalysis condition; 3), subjecting a product of step 2) to reductive amination with amino acid to obtain a final product. The application of the deguelin broken-ring structure and amino acid derivative in the preparation of antitumor drugs is also disclosed. Deguelin is structurally modified with amino acid to synthesize a drug that has the advantages of high efficiency, low toxicity, targeting property and the like, the drug is highly water-soluble and low toxic and side effect and provides significant inhibitory action for the proliferation of tumor cells, particularly the proliferation of lung cancer cells.
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Paragraph 0044
(2017/08/23)
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- Alkyne Carbonyl Metathesis As a Means to Make 4-Acyl Chromenes: Syntheses of (±)-Deguelin and (±)-Munduserone
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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
- Nayak, Maloy,Kim, Ikyon
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p. 11460 - 11467
(2015/12/01)
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- NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT
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The present invention relates to a compound inhibiting Hsp90 and a pharmaceutical composition comprising the same as an active ingredient. The compounds represented by formula 1 and formula 2 of the present invention suppress the expression of Hsp90 so that they can inhibit the accumulation of HIF-1α, the Hsp90 client protein, and also efficiently inhibit the activation of VEGF. In addition, these compounds display low cytotoxicity, so that they can be effectively used as an active ingredient of an anti-cancer agent, a diabetic retinopathy treating agent, and an anti-arthritic agent.
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Paragraph 0270-0272
(2015/07/15)
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- NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT
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The present invention relates to a novel compound inhibiting Hsp 90 and to a pharmaceutical composition including same as an active ingredient. Compounds of formula 1 and formula 2 according to the present invention inhibit the accumulation of HIF-1α protein, which is an Hsp90 client protein, by suppressing Hsp90 expression, and effectively inhibit the activity of vascular endothelial growth factor (VEGF). Furthermore, said compounds have low cytotoxicity and can thus be used as an active ingredient for the treatment of diabetic retinopathy and arthritis.
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Paragraph 0173-0175
(2015/05/26)
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- Multidimensional optimization of promising antitumor xanthone derivatives
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A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI50 of 5.1 μM, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (Kp) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log Kp between 3 and 5 and the two membrane models showed a good correlation (r2 = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues.
- Azevedo, Carlos M.G.,Afonso, Carlos M.M.,Sousa, Diana,Lima, Raquel T.,Helena Vasconcelos,Pedro, Madalena,Barbosa, Jo?o,Corrêa, Arlene G.,Reis, Salette,Pinto, Madalena M.M.
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p. 2941 - 2959
(2013/07/05)
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- Pyranoxanthones: Synthesis, growth inhibitory activity on human tumor cell lines and determination of their lipophilicity in two membrane models
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The benzopyran and dihydrobenzopyran moieties can be considered as "privileged motifs" in drug discovery being good platforms for the search of new bioactive compounds. These moieties are commonly found fused to the xanthonic scaffold belonging to the bio
- Azevedo, Carlos M.G.,Afonso, Carlos M.M.,Soares, José X.,Reis, Salette,Sousa, Diana,Lima, Raquel T.,Vasconcelos, M. Helena,Pedro, Madalena,Barbosa, Jo?o,Gales, Luís,Pinto, Madalena M.M.
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p. 798 - 816
(2013/10/22)
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- Rhodium(III)-catalyzed dehydrogenative Heck reaction of salicylaldehydes
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Your CHOice! An efficient RhIII-catalyzed dehydrogenative Heck reaction (DHR) of salicylaldehydes with different classes of olefins extends the oxidative Heck reaction to aldehyde C-H bonds. Several structural motifs similar to natural products and bioactive molecules such as aurones, flavones, 2'-hydroxychalcones, and flavanones could be efficiently produced. Initial mechanistic studies give insight into the reaction mechanism. Copyright
- Shi, Zhuangzhi,Schr?der, Nils,Glorius, Frank
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experimental part
p. 8092 - 8096
(2012/08/29)
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- Concise modular asymmetric synthesis of deguelin, tephrosin and investigation into their mode of action
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(Figure Presented) The concise nature and modularity of the synthesis described for deguelin and tephrosin (retrosynthetic analysis depicted) should facilitate access to labeled analogues to dissect the mechanism of action of this important pharmacophore.
- Garcia, Jose,Barluenga, Sofia,Beebe, Kristin,Neckers, Len,Winssinger, Nicolas
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supporting information; experimental part
p. 9767 - 9771
(2010/10/21)
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- Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II
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Herein is reported an efficient method for the synthesis of 2,2-dimethyl-2H-chromenes in a single step from the corresponding phenol and 3-methyl-2-butenal via microwave irradiation in CDCl3. This protocol features a mild reaction environment (neutral, no added catalyst) which yields regioselective formation of the chromene and displays tolerance toward acid- and base-sensitive protecting groups.
- Adler, Marc J.,Baldwin, Steven W.
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supporting information; experimental part
p. 5075 - 5079
(2009/12/01)
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- A concise route for the synthesis of biologically interesting pyranocoumarins - Seselin, (±)-cis-khellactone, (±)- quianhucoumarin D, and the (±)-5-deoxyprotobruceol-I regioisomer
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An efficient synthesis of pyranocoumarins is achieved starting from 2H-pyrans. This process provides naturally occurring seselin, cis-khellactone, quianhucoumarin D, and the 5-deoxyprotobruceol-I regioisomer. Georg Thieme Verlag Stuttgart.
- Lee, Yong Rok,Lee, Won Kyong,Noh, Seok Kyun,Lyoo, Won Seok
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p. 853 - 859
(2007/10/03)
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- Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans
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Herein we report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran moiety is selected as an inaugural template for the construction of natural product-like libraries via this strategy. Initially, a novel solid-phase synthesis of the benzopyran motif is developed employing a unique cycloloading strategy that relies on the use of a new, polystyrene-based selenenyl bromide resin. Once the loading, elaboration, and cleavage of these benzopyrans was established, this new solid-phase method was then thoroughly validated through the construction of six focused combinatorial libraries designed around natural and designed molecules of recent biological interest.
- Nicolaou,Pfefferkorn,Roecker,Cao,Barluenga,Mitchell
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p. 9939 - 9953
(2007/10/03)
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- Asymmetric Solid-Phase Synthesis of (3′R,4′R)-Di-O-cis-acyl 3-Carboxyl Khellactones
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Matrix Presented We describe a practical parallel synthesis of (3′R,4′R)-di-O-cis-acyl 3-carboxyl khellactones on a solid phase in high yield. The highlights of this synthesis include a Knoevenagel condensation, asymmetric dihydroxylation, catalyzed acylation, and product cleavage from the solid support.
- Xia, Yi,Yang, Zheng-Yu,Brossi, Arnold,Lee, Kuo-Hsiung
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p. 2113 - 2115
(2008/02/09)
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- Microwave-assisted rate-enhanced method for the synthesis of 2,2- dimethyl-2H-chromenes
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Herein we describe a simple and facile method for the synthesis of chromenes by base catalyzed condensation of phenols with 3-methyl-2-butenal under microwave irradiation.
- Subburaj, Kandasamy,Trivedi, Girish K.
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p. 259 - 263
(2007/10/03)
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- Synthesis of the Phytoalexin (+/-)-Phaseollin: 3-Phenylthiochromans as Masked 2H-Chromenes and o-Prenyl Phenols
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Phenylthiyl radicals are shown to add regiospecifically to 2H-chromenes to afford 3-phenylthiochromans (8), (10), (13), (14), and (15).The sulphide (15), as equivalent to a chromene protected against acid and oxidation, has been used in two syntheses of (+/-)-phaseollin, a major phytoalexin of beans and other legumes, via the sequence (17)->(18)->(19)->(20)->(21)->(+/-)-(1) or (19)->(22)->(23)->(+/-)-(1).Also the 3-phenylthiochromans, on electron transfer from metal naphthalenide or a mercury cathode, open to o-prenylphenols, providing a two step route to biogenetically important phenols from chromenes which is tolerant of free phenol and carbonyl functions and trisubstituted double bonds.
- Mohamed, Salah E. N.,Thomas, Philip,Whiting, Donald A.
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p. 431 - 438
(2007/10/02)
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- SYNTHESIS OF (+/-)-PHASEOLLIN; A PROTECTIVE SEQUENCE FOR CHROMEN DOUBLE BONDS
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(+/)-Phaseollin, an important phytoalexin, has been synthesised, using as key step thallium III induced rearrangement of chromenochalcone (6) and proceeding via (8).The chromene double bond can be efficiently protected from thalliation by regioselective radical addition of thiophenol.An alternative route to phaseollin is given, through (12)-(14)-(1), with regeneration of the double bond by pyrolysis of the sulphoxide of (15).
- Thomas, Phillip,Whiting, Donald A.
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p. 1099 - 1102
(2007/10/02)
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- CONSTITUENT OF THE CHINESE CRUDE DRUG "SANG-BAI-PI" (MORUS ROOT BARKS) III. STRUCTURE OF A NEW FLAVANONE DERIVATIVE, SANGGENON F.
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From the benzene extract of the Chinese crude drug "Sang-Bai-Pi" (Japanese name "Sohakuhi"), the root barks of Morus sp. (Moraceae), an isoprene substituted flavanone derivative, named sanggenon F, was isolated, for which stucture (I) was proposed on the basis of its spectral and chemical evidence.
- Nomura, Taro,Fukai, Toshio,Hano, Yoshio,Tsukamoto, Koji
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p. 661 - 666
(2007/10/02)
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