111462-38-5Relevant academic research and scientific papers
Total synthesis and the anticancer activity of (+)-spisulosine
Fabi?íková, Milica,Martinková, Miroslava,Hirková, Simona,Gonda, Jozef,Pilátová, Martina Bago,G?nciová, Gabriela
, p. 26 - 36 (2016/10/04)
The total synthesis of the anticancer agent (+)-spisulosine has been accomplished. The strategy involved a substrate-controlled aza-Claisen rearrangement to establish the erythro-configured amino-alcohol motif followed by deoxygenation to create a methyl
Hydrophobic substituents increase the potency of salacinol, a potent α-glucosidase inhibitor from Ayurvedic traditional medicine ‘Salacia’
Tanabe, Genzoh,Xie, Weijia,Balakishan, Gorre,Amer, Mumen F.A.,Tsutsui, Nozomi,Takemura, Haruka,Nakamura, Shinya,Akaki, Junji,Ninomiya, Kiyofumi,Morikawa, Toshio,Nakanishi, Isao,Muraoka, Osamu
, p. 3705 - 3715 (2016/07/20)
Using an in silico method, seven analogs bearing hydrophobic substituents (8a: Me, 8b: Et, 8c: n-Pent, 8d: n-Hept, 8e: n-Tridec, 8f: isoBu and 8g: neoPent) at the 3′-O-position in salacinol (1), a highly potent natural α-glucosidase inhibitor from Ayurvedic traditional medicine ‘Salacia’, were designed and synthesized. In order to verify the computational SAR assessments, their α-glucosidase inhibitory activities were evaluated in vitro. All analogs (8a–8g) exhibited an equal or considerably higher level of inhibitory activity against rat small intestinal α-glucosidases compared with the original sulfonate (1), and were as potent as or higher in potency than the clinically used anti-diabetics, voglibose, acarbose or miglitol. Their activities against human maltase exhibited good relationships to the results obtained with enzymes of rat origin. Among the designed compounds, the one with a 3′-O-neopentyl moiety (8g) was most potent, with an approximately ten fold increase in activity against human maltase compared to 1.
CYCLIC SULFONIUM SALT, PROCESS FOR PRODUCTION OF SAME, AND alpha-GLUCOSIDASE INHIBITOR COMPRISING SAME
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Paragraph 0090-0092, (2014/01/08)
Provided is a novel cyclic sulfonium salt compound which is useful for the prevention or treatment of diabetes and the like. The present invention relates to a novel cyclic sulfonium salt compound represented by general formula (I) or (II), an isomer or solvate of the compound, or a pharmaceutically acceptable salt of the compound or the isomer or solvate. The present invention also relates to an α-glucosidase inhibitor, a pharmaceutical composition for preventing or treating diabetes, and an anti-diabetes food, each of which comprises the compound represented by general formula (I) or (II) and the like.
Biological evaluation of 3′-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3′ position in the side chain on the α-glucosidase inhibitory activity
Tanabe, Genzoh,Otani, Tetsu,Cong, Wenying,Minematsu, Toshie,Ninomiya, Kiyofumi,Yoshikawa, Masayuki,Muraoka, Osamu
scheme or table, p. 3159 - 3162 (2011/06/26)
Four analogs with 3′-O-alkyl groups (9a: CH3, 9b: C 2H5, 9c: C13H27 or 9d: CH 2Ph) instead of the 3′-O-sulfate anion in salacinol (1), a naturally occurring potent α-glucosidase inhibitor, were synthesized by the coupling reaction of 1,4-dideoxy-1,4-epithio-d-arabinitols (18a and 18b) with appropriate epoxides (10a-10d). These analogs showed equal or considerably higher inhibitory activity against rat small intestinal α-glucosidases than the original sulfate (1), and one of them (9d) was found more potent than currently used α-glucosidase inhibitors as antidiabetics. Thus, introduction of a hydrophobic moiety at the C3′ position of this new class of inhibitor was found beneficial for onset of stronger inhibition against these enzymes.
The formal synthesis of 3-epi jaspine B using stereoselective intramolecular oxa-Michael addition
Rao, G. Srinivas,Sudhakar, Neela,Rao, B. Venkateswara,Basha, S. Jeelani
experimental part, p. 1963 - 1970 (2010/10/18)
The formal synthesis of 3-epi jaspine B was achieved by using a stereoselective intramolecular oxa-Michael addition. The diacetate derivative of 3-epi jaspine B was also synthesized.
Convenient enantiopure synthesis of (2S,3R)-2-O-benzyl-3,4-O- isopropylidene-D-erythritol from D-(+)-glucono-δ-lactone: A potential C4 chiral building block
Vijayasaradhi, Sivalenka,Beedimane, Manjunath Narayana,Aidhen, Indrapal Singh
, p. 2267 - 2269 (2007/10/03)
A new convenient synthesis of (2S,3R)-2-O-benzyl-3,4-O-isopropylidene-D- erythritol has been achieved starting from extremely cheap and commercially available D-(+)-glucono-δ-lactone. It involves two carbon excisions using ozonolysis. The inbuilt stereoch
Enantioselective synthesis of ethyl 4,5,7,8,9-penta-O-acetyl-2,6- anhydro-3-deoxy-D-erythro-L-gluca-nononate: A 2-monodeoxygenated derivative of '2-keto-3-deoxy-D-glycero-D-galacto-nononic acid'
Shen, Xin,Wu, Yu-Lin,Wu, Yikang
, p. 943 - 953 (2007/10/03)
A study aimed at developing an enantioselective synthesis of the title compound 23, a 2-monodeoxy analogue of the naturally occurring (+)-2-keto-3- deoxy-D-glycero-D-galacto-2-nononic acid (KDN), is reported. From D-mannose as starting material, the chiral 1,3-diene 10, activated by a silyloxy substituent at C(2), was prepared in six steps (Scheme 1). However, the intermediates were often contaminated with varying amounts of by-products arising from overoxidation during cleavage with periodic acid. An alternative route starting from the inexpensive and readily available D-isoascorbic acid (12), though a little longer than the first, satisfactorily circumvented the purification problem and led to the desired dienes 17 in good yields (scheme 2). The [Co11(S,S)-(+)-salen]-catalyzed hetero-Diels-Alder reactions of the aforementioned dienes with ethyl glyoxylate proceeded smoothly at room temperature, giving the dihydropyrano adducts 18 in moderate yields (Scheme 3). Dihydroxylation of 18a followed by reduction of the keto function gave the desired 4,5-trans dihydroxy moiety of the KDN framework (Scheme 4, see 21). The spectroscopic data of the penta-O-acetylated 2-deoxy-KDN ethyl ester 23 were consistent with those reported for the corresponding methyl ester derived from natural KDN.
A Straightforward Preparation of Both Enantiomerically Pure 2-O-Benzyl-erythro-Butanetetrols
Flasche, Michael,Scharf, Hans-Dieter
, p. 1543 - 1546 (2007/10/02)
A short and efficient synthesis of both enatiomerically pure 2-O-benzyl-erythro-butanetetrols 4 and ent-4 from the readily available D-erthronolactone 1 is presented.The synthesis proceeds in a highly efficient manner and is in both cases substrate controlled.
Diastereoselective addition of lower order vinylcuprates to (R)-2,3-O-isopropylideneglyceraldehyde
Metz,Schoop
, p. 10597 - 10608 (2007/10/02)
Highly syn or anti selective addition of lower order lithium vinylcuprates generated from alkenyl bromides 1 to (R)-2,3-O-isopropylideneglyceraldehyde (2) can be achieved, respectively, depending on the substitution pattern of the vinyl moiety and the solvent. α-Trimethylsilyl substituted vinylcuprates possessing an alkyl substituent Z to copper react with excellent syn selectivity in ether whereas a highly anti selective addition is observed for cuprates bearing a hydrogen atom Z or α to the metal in THF. A model is proposed to rationalize these complementary selectivities.
Preferred Conformation of C-Glycosides. 8. Synthesis of 1,4-Linked Carbon Disaccharides
Wang, Yuan,Babirad, Stefan A.,Kishi, Yoshito
, p. 468 - 481 (2007/10/02)
Three general synthetic routes to 1,4-linked carbon disaccharides (e.g., 3, 4, 15-17, 21-23, 44, and 45) are presented.Control of the stereochemistry at C.1', C.2', C.5'and C.4, the incorporation of deuterium labels at the C.α position, and structural mod
