848081-07-2Relevant academic research and scientific papers
A Concise Enantiodivergent Synthesis of Equol
Uemura, Takahito,Saito, Yusuke,Sonoda, Motohiro,Tanimori, Shinji
supporting information, p. 693 - 696 (2020/12/23)
Equol, a nonsteroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein, has been synthesized as both enantioenriched forms based on MacMillan's α-Arylation of carbonyl compound mediated by amino acid derived indazolidinones and copper precatalysts. The natural form of (S)-equol and its enantiomer (R)-equol have been synthesized in 8 steps from 2,4-dimethoxybenzaldehyde with good enantiomeric purity (90% ee and 90% ee, respectively).
H-type zeolite-catalyzed 1,4-addition of benzene derivatives to labile acrolein
Hayashi, Daijiro,Narisawa, Tomoyuki,Masui, Yoichi,Onaka, Makoto
, p. 460 - 471 (2016/04/26)
The 1,4-addition of benzene derivatives to acrolein is a straightforward way to synthesize 3-arylpropanals. A survey of acid catalysts for the 1,4-addition of methoxy-substituted benzenes to acrolein revealed that H-Beta and H-Y were the most suitable catalysts. We hypothesized three side-reactions: (1) the double 1,4-addition of acrolein to the starting benzene derivatives, (2) the Friedel-Crafts-type alkylation to the desired product, and (3) the self-polymerization of acrolein. The type (3) side-reaction was inhibited by two different methods which kept the concentration of acrolein low in the reaction mixture or in the zeolite pores. First, acrolein monomers were in situ generated through the gradual monomerization of an acrolein cyclic trimer. Second, using a reaction solvent lowered the acrolein concentration in the zeolite pores due to the competitive adsorption. We discovered that the content of monomeric acrolein in a solvent was closely related to the polarity of the solvent. Actually, both methods improved the yields for the 1,4-additions of 1,3-dimethoxybenzene to acrolein. Other electron-rich benzene derivatives, such as phenol and N, N-dimethylaniline, were also applicable to the 1,4-addition reactions.
5,6,7,8-TETRAHYDRO-IMIDAZO[1,5-A]PYRAZINE DERIVATIVES
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Page/Page column 55, (2008/12/06)
The invention relates to 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine derivatives of formula (I),wherein X represents CH2 or O; R1 represents a phenyl group, which group is independently mono-, di-, or tri-substituted wherein the substituents are independently selected from the group consisting of (C1-4)alkyl, (C1-4)alkoxy, halogen, cyano, trifluoromethoxy and trifluoromethyl; R2 represents (C1-4)alkyl, (C1-4)alkoxy, (C2-4)alkenyl, halogen, cyano, hydroxymethyl, trifluoromethyl, C(O)NR5R6 or cyclopropyl; R3 represents (C1-4)alkyl, (C1-4)alkoxy-methyl or halogen; R4 represents (C1-4)alkyl; R5 represents hydrogen or (C1-4)alkyl; and R6 represents hydrogen or (C1-4)alkyl. The invention also relates to pharmaceutically acceptable salts of such compounds; and to the use of such compounds as medicaments; especially as orexin receptor antagonists.
Synthesis of classical and nonclassical 2-amino-4-oxo-6-benzylthieno-[2,3- d]pyrimidines as potential thymidylate synthase inhibitors
Gangjee, Aleem,Qiu, Yibin,Kisliuk, Roy L.
, p. 941 - 946 (2007/10/03)
A series of seven nonclassical 2-amino-4-oxo-6-substituted thieno[2,3-d]pyrimidines 2-8 and one classical N-[4-(2-amino-4-oxo-3,4- dihydrothieno[2,3-d]pyrimidin-6-ylmethyl)benzoyl]-L-glutamic acid 9 (Table I) were designed as the first in a series of 6-substituted 6-5 fused ring analogs as potential thymidylate synthase (TS) inhibitors and as antitumor agents. The target compounds were synthesized via a Heck coupling of appropriately substituted iodobenzenes and allyl alcohol followed by cyclization using cyanoacetate and sulfur powder to afford substituted thiophenes. The resulting thiophenes were then cyclocondensed with chloroformamidine hydrochloride to afford 2-amino-4-oxo-6-substituted thieno[2,3-d]pyrimidines 2-8 and 26. Hydrolysis of 26 followed by coupling with diethyl L-glutamate afforded 28. The classical analog 9 was obtained by hydrolysis of 28. None of the target compounds inhibited human recombinant thymidylate synthase at 23 μM except 9 for which the IC50 value was 100 μM.
