On the contents of schumanniophyton problematicum (rubiaceae)

Section: Chromones Annelated With a System Of Two Condensed Heterocyclesmentioning

confidence: 99%

Synthesis and biological activity of chromones annelated at the C(7)–C(8) bond with heterocycles (review)

Лозинский

Shokol

Khilya

2011

“…It enters into the composition of the pyridylchromone alkaloid schumanniophytin, isolated from the roots and bark of Schumanniophyton magnificum and S. problematicum [5][6][7].It is known that α-pyrono[2,3-f]flavones and isoflavones display bactericidal activity [8]. The same activity is also found for 2-hetarylpyrano[2,3-f]chromene-4,8-diones, including furyl analogs of α-pyrono-[2,3-f]flavones [9], which arouses interest in heterocyclic derivatives of this system.…”

mentioning

confidence: 99%

“…It enters into the composition of the pyridylchromone alkaloid schumanniophytin, isolated from the roots and bark of Schumanniophyton magnificum and S. problematicum [5][6][7].…”

mentioning

confidence: 99%

Furyl analogs of α-pyrono[2,3-f]isoflavones with an azole substituent in the α-pyrone nucleus

Shokol

Лозинский

Tkachuk

et al. 2010

The pyrano[2,3-f]chromene-4,8-dione system is the basis of the natural compounds clauzenidine [1,2] and calomelanol D [3,4]. It enters into the composition of the pyridylchromone alkaloid schumanniophytin, isolated from the roots and bark of Schumanniophyton magnificum and S. problematicum [5][6][7].It is known that α-pyrono[2,3-f]flavones and isoflavones display bactericidal activity [8]. The same activity is also found for 2-hetarylpyrano[2,3-f]chromene-4,8-diones, including furyl analogs of α-pyrono-[2,3-f]flavones [9], which arouses interest in heterocyclic derivatives of this system.As a continuation of our investigations in the area of heterocyclic analogs of isoflavones [10] and complex flavonoids [11,12], in the present work we have synthesized furyl analogs of α-pyrono-[2,3-f]isoflavones containing azole substituents in position 9 of the molecule.3-Furyl-7-hydroxychromones 1 and 2 were used as starting compounds, and were formylated with hexamethylenetetramine in acetic acid according to the Daff reaction. The formation of the corresponding 8-formyl-substituted products 3 and 4 (Table 1) was confirmed by the absence from the 1 H NMR spectra of these compounds, recorded in DMSO-d 6 , of the singlet of the H-8 proton at 6.79 ppm characteristic of the initial chromones 1 and 2 ( Table 2). The singlet of the formyl group proton was found at 10.48-10.52 ppm, and the signal of the OH group proton was displaced relative to the analogous signal of compounds 1 and 2 by almost 2 ppm towards low field, as the result of the formation of a chelated intramolecular hydrogen bond. Confirmation of the chelate structure of compounds 3 and 4 is their red-brown coloration with an alcoholic solution of iron(III) chloride and the presence of a broad band at 3080-3090 cm -1 in their IR spectra.

“…Thus, in a continuation of a study of the synthesis and properties of coumarin heteroanalogs, we investigated the preparation and reactivity of substituted 4-(3-amino-2-benzofuranyl)-coumarins. Special interest was found in the synthesis of condensed derivatives of pyridino[3,4-c]coumarins since such alkaloids have been isolated from Schumanniophyton problematicum [10]. Many alkaloids are known to be very valuable pharmaceutical products or serve as starting materials for the synthesis of such products.…”

mentioning

confidence: 99%

Synthesis and properties of 4-(3-amino-2-benzofuranyl)-coumarins

Frasinyuk

Gorelov

Bondarenko

et al. 2009

The healing properties of many plants have been long known and their present use is continuing to increase since an advantage of plant preparations is their low toxicity and the possibility of using them for long periods without the risk of side-reactions. The major groups of therapeutically active plants are alkaloids, steroid glycosides, saponins, flavonoids, coumarins, organic acids, and vitamins.Derivatives of oxygen heterocycles are among the most common classes of natural products [1]. Compounds containing two or more oxygen heterocycles are encountered in nature much less frequently. Some of the most important such compounds are furocoumarins [2], linear and angular furochromones, coumestans, rotenoids [3], and coumarin and flavonoid derivatives containing a pyran ring fused to ring A or B [4,5].Coumarin derivatives containing a benzofuran ring possess anti-inflammatory, hypotensive, and analgesic action [6-9]. Thus, in a continuation of a study of the synthesis and properties of coumarin heteroanalogs, we investigated the preparation and reactivity of substituted 4-(3-amino-2-benzofuranyl)-coumarins. Special interest was found in the synthesis of condensed derivatives of pyridino[3,4-c]coumarins since such alkaloids have been isolated from Schumanniophyton problematicum [10]. Many alkaloids are known to be very valuable pharmaceutical products or serve as starting materials for the synthesis of such products.The alkylation of salicylonitrile by 4-bromomethylcoumarin in acetone in the presence of potassium carbonate at room temperature leads to 4-(2-cyanophenoxymethoxy)coumarins, which are converted upon heating in ethanol at reflux in the presence of potassium carbonate into 4-(3-amino-2-benzofuranyl)coumarins [9].