Horsfiline, an oxindole alkaloid from Horsfieldia superba

Crystal structure of 2-spiro-3′-(2-oxindole)-3-benzoyl-4-phenyl-5- hydroxymethylpyrrolidine, C25H22N2O3

“…Spiro[pyrrolidine-2,3'-oxindole] ring system is as tructural feature found in aw ide variety of oxindole alkaloids, such as horsfiline 1 [1] and spirotryprostatin B [2], which have been reported to behave as aldose reductase, poliovirus, and rhinovirus 3C-proteinase inhibitors [3]. The 1,3-dipolar cycloaddition reaction has also been employed for the construction of spiro-[pyrrolidine-2,3'-oxindoline] derivatives.…”

Design and synthesis of spiro derivatives containing a thiophene ring and evaluation of their Anti-microbial activity

“…11 1,3-dipolar cycloaddition reactions of azomethineylides has been well developed, and also the reactions proceed with high regio-and stereoselectivity 12,13 . Thiophene and its derivatives are the significant class of heterocyclic compounds possessing broad biological activities, such as antiinflammatory 14 , analgesic 14 , antioxidant 15 , antitubercular, 16 antidepressant, 17 sedative, 18 antiamoebic, 19 oral analgesic, 20 anti-metabolite, 21 and antineoplastic properties. 22 For a extended analysis of the regiochemistry in 1,3-dipolar cycloaddition reaction and also the bioactivity of spiro [pyrrolidine-2,3'-oxindoline] compounds, three varieties of trapping agents like dipolarophiles, diketone, -amino acid, were introduced during this reaction to synthesis a series of spiro [pyrrolidine-2,3'-oxindole] derivatives, with that the bioactivity on anti-microbial activity was evaluated.…”

Facile access to regio- and stereoselective synthesis of highly functionalized spiro[indoline-3,2′-pyrrolidines] incorporating a pyrene moiety: experimental, photophysical and theoretical approach

“…3 The spiro pyrrolidine-oxindole system is the core structure of several natural alkaloids and pharmacological agents such as spirotryptostatine A and B, 4 elacomine, 5 horsiline, 6 and coreleucine.…”

“…19 However, there is little published work regarding the synthesis of spiroheterocyclic compounds which incorporate the pyrene moiety. 20 Herein, as a part of our research program on [3 + 2] cycloaddition reactions, 20,21 we describe the results of experimental and theoretical studies on the stereo-and regioselectivity of the [3 + 2] cycloaddition reaction of azomethine ylides, generated in situ from isatin (1) and sarcosine (2) or benzylamine (6), to a series of (E)-3-aryl-1-(pyren-1-yl)prop-2-en-1-ones 3a-f to afford a new series of 4 0 -aryl-3'-(pyrene-1-carbonyl)spiro[indoline-3,2 0 -pyrrolidin]-2-ones 4a-f.…”