94124-45-5Relevant academic research and scientific papers
An Intramolecular Iodine-Catalyzed C(sp3)?H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans
Br?se, Stefan,Koch, Vanessa
supporting information, p. 3478 - 3483 (2021/07/22)
The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C?H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)?H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.
Development of Hybrid Phospholipid Mimics as Effective Agonists for Liver Receptor Homologue-1
Flynn, Autumn R.,Mays, Suzanne G.,Ortlund, Eric A.,Jui, Nathan T.
supporting information, p. 1051 - 1056 (2018/09/21)
The orphan nuclear receptor Liver Receptor Homologue-1 (LRH-1) is an emerging drug target for metabolic disorders. The most effective known LRH-1 modulators are phospholipids or synthetic hexahydropentalene compounds. While both classes have micromolar ef
Total Synthesis of the Proposed Structures of the Novel Antimalarial Pyranone Cryptorigidifoliol e
Manikanta, Gembali,Nagaraju, Tumula,Radha Krishna, Palakodety
, p. 4213 - 4220 (2016/11/26)
The total syntheses of the proposed structures of the antimalarial lactone cryptorigidifoliol E are described. The synthetic sequence notably features a Bartlett-Smith halocyclization to give a chiral epoxide, followed by its regioselective ring-opening r
Bongkrekic Acid Analogue, Lacking One of the Carboxylic Groups of its Parent Compound, Shows Moderate but pH-insensitive Inhibitory Effects on the Mitochondrial ADP/ATP Carrier
Yamamoto, Atsushi,Hasui, Keisuke,Matsuo, Hiroshi,Okuda, Katsuhiro,Abe, Masato,Matsumoto, Kenji,Harada, Kazuki,Yoshimura, Yuya,Yamamoto, Takenori,Ohkura, Kazuto,Shindo, Mitsuru,Shinohara, Yasuo
, p. 1304 - 1322 (2015/10/28)
Bongkrekic acid, isolated from Burkholderia cocovenenans, is known to specifically inhibit the mitochondrial ADP/ATP carrier. However, the manner of its interaction with the carrier remains elusive. In this study, we tested the inhibitory effects of 17 bo
Molecular design, synthesis, and evaluation of novel potent apoptosis inhibitors inspired from bongkrekic acid
Okuda, Katsuhiro,Hasui, Keisuke,Abe, Masato,Matsumoto, Kenji,Shindo, Mitsuru
, p. 2253 - 2260 (2013/01/15)
Bongkrekic acid (BKA) is an inhibitor of adenine nucleotide translocase (ANT). Since inhibition of ANT is connected to the inhibition of cytochrome c release from mitochondria, which then results in the suppression of apoptosis, it has been used as a tool for the mechanistic investigation of apoptosis. BKA consists of a long carbon chain with two asymmetric centers, a nonconjugated olefin, two conjugated dienes, three methyl groups, a methoxyl group, and three carboxylic acids. This complicated chemical structure has caused difficulties in synthesis, supply, and biochemical mechanistic investigations. In this study, we designed and synthesized more simple tricarboxylic acids that were inspired by the molecular structure of BKA. Their cytotoxicity and apoptosis-preventing activity in HeLa cells and the effect on the mitochondrial inner membrane potential (Δψm) in HL-60 cells were then evaluated. All tested tricarboxylic acid derivatives including BKA showed little toxicity against HeLa cells. BKA and two of the synthesized derivatives significantly suppressed staurosporine (STS)-induced reductions in cell viability. Furthermore, STS-induced Δψm collapse was significantly restored by pretreatment with BKA and a tricarboxylic acid derivative. Other derivatives, in which one of three carboxylic acids was esterified, exhibited potent toxicity, especially a derivative bearing a carbon chain of the same length as that of BKA. In conclusion, we have developed a new lead compound as an apoptosis inhibitor bearing three carboxylic acids connected with the proper length of a long carbon chain.
Development of a concise and diversity-oriented approach for the synthesis of plecomacrolides via the diene-ene RCM
Lu, Kui,Huang, Mengwei,Xiang, Zheng,Liu, Yongxiang,Chen, Jiahua,Yang, Zhen
, p. 1193 - 1196 (2007/10/03)
A concise synthesis of the core structures of plecomacrolide with ring sizes varying from 16 to 19 atoms was achieved for the first time by the diene-ene ring-closing olefin metathesis reaction. This approach should allow access to the structurally divers
Synthesis of oligogalacturonates conjugated to BSA
Clausen, Mads,Madsen, Robert
, p. 2159 - 2169 (2007/10/03)
The synthesis of three oligogalacturonates with an aldehyde spacer attached at the reducing end is described. Trigalacturonates α-D-GalpA-(1→4)- α-D-GalpA-(1→4)-α-D-GalpA-(1→O(CH2) 7CHO and α-D-GalpA(Me)-(1→4)-α-D-GalpA(Me)- (1→4)-α-
A catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol is a good combination for the cleavage of tetrahydropyranyl (THP) and tert-butyldimethylsilyl (TBS) ethers
Khan, Abu T.,Islam, Samimul,Choudhury, Lokman H.,Ghosh, Subrata
, p. 9617 - 9621 (2007/10/03)
Various THP and TBS ethers can be unmasked easily to the corresponding hydroxyl compounds in good yields by using a combination of a catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol at room temperature. In addition, alkyl TBS ethers can be hydrolyzed chemoselectively in the presence of aryl TBS ethers. Moreover, alkyl TBS ethers can be cleaved easily in the presence of alkyl or aryl THP ethers using the same conditions.
A simple and useful synthetic protocol for selective deprotection of tert-butyldimethylsilyl (TBS) ethers
Khan, Abu T.,Ghosh, Subrata,Choudhury, Lokman H.
, p. 2198 - 2204 (2007/10/03)
A wide variety of tert-butyldimethylsilyl ethers 1 can be easily cleaved to the corresponding parent hydroxyl compound 2 in the presence of 5 mol % of acetonyltriphenylphosphonium bromide (ATPB) at room temperature. In addition, tert-butyldiphenylsilyl ethers can also be cleaved by using 20 mol % of the same catalyst. Alkyl tert-butyldimethylsilyl ethers can be deprotected to the hydroxyl compounds chemoselectively in the presence of aryl tert- butyldimethylsilyl ethers. Some of the major advantages are mild reaction conditions, no aqueous workup, high efficiency and chemoselectivity and compatibility with other protecting groups; no brominations occur in the aromatic ring under these experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Differential cleavage of arylmethyl ethers: Reactivity of 2,6-dimethoxybenzyl ethers
Falck,Barma,Baati, Rachid,Mioskowski, Charles
, p. 1281 - 1283 (2007/10/03)
CrCl2/LiI selectively cleave benzyl ethers and methoxy-substituted benzyl ethers (see scheme) in the order: C6H5CH2OR 6H4CH2OR 2C6H3CH2OR 2C6H3CH2OR. In contrast, C6H5CH2OR is more readily cleaved than 2,6-(MeO)2C6H3CH2OR during catalytic hydrogenolysis while 3,4-(MeO)2C6H3CH2OR is cleaved faster than 2,6-(MeO)2C6H3CH2OR with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).
