Circumdatin A, B, and C:  Three New Benzodiazepine Alkaloids Isolated from a Culture of the Fungus <i>Aspergillus ochraceus</i>

Rahbæk, Lisa; Breinholt, Jens; Frisvad, Jens Christian; Christophersen, Carsten

doi:10.1021/jo981536u

Cited by 105 publications

(76 citation statements)

References 18 publications

(16 reference statements)

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“…Comparison of 1D-and 2D-NMR spectral data of 1 with those of circumdatin C (4) [1] revealed that the structures of these two compounds are very similar. However, the Helvetica Chimica Acta -Vol.…”

Section: Benzodiazepine Alkaloids From Marine-derived Endophytic Fungusmentioning

confidence: 96%

“…By comparison of their NMR data with those reported in the literature, their structures were determined as circumdatin F (3) [2], circumdatin C (4) [1], circumdatin D (5) [2], notoamide B (6) [11], and selerotiamide (7) [12].…”

Section: Benzodiazepine Alkaloids From Marine-derived Endophytic Fungusmentioning

confidence: 96%

“…Aspergillus ochraceus A new fungus-derived benzodiazepine analogue, 2-hydroxycircumdatin C (1), and a compound which has been isolated from a natural resource for the first time, but has been previously synthesized, namely (11aS)-2,3-dihydro-7-methoxy-1H-pyrrolo[2,1-c] [1,4]benzodiazepine-5,11(10H,11aH)-dione (2), along with five structurally related known alkaloids (3 -7), were isolated from Aspergillus ochraceus, an endophytic fungus derived from the marine brown alga Sargassum kjellmanianum. Their structures were established on the basis of spectroscopic methods.…”

Section: Benzodiazepine Alkaloids From Marine-derived Endophytic Fungusmentioning

confidence: 99%

“…Our continuing investigation on the subject has led to the identification of seven alkaloids from Aspergillus ochraceus EN-31, an endophytic fungus obtained from the marine brown alga Sargassum kjellmanianum. The identified compounds include one new compound 2-hydroxycircumdatin C (1), one compound that has been isolated from a natural source for the first time, but has been previously synthesized, (11aS)-2,3-dihydro-7-methoxy-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione (2) [10], as well as the five known compounds circumdatin F (3) [2], circumdatin C (4) [1], circumdatin D (5) [2], notoamide B (6) [11], and selerotiamide (7) [12]. Herein, we report the isolation, structure determination, and DPPH radical-scavenging activity of the new compound, 6-hydroxycircumdatin C (1).…”

Section: Benzodiazepine Alkaloids From Marine-derived Endophytic Fungusmentioning

confidence: 99%

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Benzodiazepine Alkaloids from Marine‐Derived Endophytic Fungus Aspergillus ochraceus

Cui

et al. 2009

Helvetica Chimica Acta

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A new fungus-derived benzodiazepine analogue, 2-hydroxycircumdatin C (1), and a compound which has been isolated from a natural resource for the first time, but has been previously synthesized,, along with five structurally related known alkaloids (3 -7), were isolated from Aspergillus ochraceus, an endophytic fungus derived from the marine brown alga Sargassum kjellmanianum. Their structures were established on the basis of spectroscopic methods. The absolute configuration of 1 was determined through CD evidence. Compound 1 displayed significant DPPH radical-scavenging activity with an IC 50 value of 9.9 mm, which is 8.9-fold more potent than that of butylated hydroxytoluene (BHT), a well-known synthetic positive control.

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Section: Benzodiazepine Alkaloids From Marine-derived Endophytic Fungusmentioning

confidence: 96%

Section: Benzodiazepine Alkaloids From Marine-derived Endophytic Fungusmentioning

confidence: 96%

Section: Benzodiazepine Alkaloids From Marine-derived Endophytic Fungusmentioning

confidence: 99%

Section: Benzodiazepine Alkaloids From Marine-derived Endophytic Fungusmentioning

confidence: 99%

See 2 more Smart Citations

Benzodiazepine Alkaloids from Marine‐Derived Endophytic Fungus Aspergillus ochraceus

Cui

et al. 2009

Helvetica Chimica Acta

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“…For puckering and asymmetry parameters, see : Cremer & Pople (1975);Nardelli (1983). For the use of benzodiazepines in the treatment of gastrointestinal and central nervous system disorders, see: Rahbaek et al (1999).…”

Section: Related Literaturementioning

confidence: 99%

5-Chloroacetyl-4-methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Ravichandran

Sakthivel²,

Ponnuswamy³

et al. 2009

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.002 Å; R factor = 0.043; wR factor = 0.128; data-to-parameter ratio = 25.7.In the title compound, C 12 H 13 ClN 2 O 2 , the benzodiazepine ring adopts a distorted boat conformation. The carbonyl O atom and the Cl atom of the chloroacetyl group are in a cis conformation. The crystal packing is controlled by intermolecular C-HÁ Á ÁO and N-HÁ Á ÁO interactions. Related literature

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Carboamination and Alkylative Cyclization withCNBond Formation in Stereoselective Syntheses

Ghorai

Halder

Samanta

2013

Stereoselective Synthesis of Drugs and Natural Products

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The carboamination reaction can be considered an important and fascinating tool for atom‐economic and convergent construction toward the functionalized N ‐containing cyclic compounds. Because the aza‐cycle is frequently found in almost all members of the alkaloid family with immense synthetic and pharmacological activities, the formation of this ring system is a highly demanding task for synthetic organic chemists. As a result, several rational techniques have been developed including intramolecular S N 2 reactions, reductive amination reactions, conjugate addition reactions, metal‐ and acid‐catalyzed cyclizations, and ring‐closing olefin metathesis reactions. Despite the many available routes, the carboamination strategy could be one of the best techniques considering stereoselectivity and the step economic path toward the formation of ring compounds in an elegant way.Alkylative cyclization with CN bond formation ( N ‐alkylation) is one of the most important methods in organic synthesis for the construction of aza‐cycles. Many well‐known name reactions (e.g., aza‐Diels‐Alder, aza‐Michael, aza‐Mannich, aza‐Henry reactions, etc.), which are generally being employed in the intramolecular CN bond formation step, can be treated as CN alkylative cyclization. It is an extremely powerful method for the stereoselective synthesis of N ‐heterocycles like aziridines, azetidines, lactams, pyrrolidines, piperidines, amino sugars, and many more, which are the basic structural units present in many natural products and biologically active compounds.

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Circumdatin A, B, and C: Three New Benzodiazepine Alkaloids Isolated from a Culture of the Fungus Aspergillus ochraceus

Cited by 105 publications

References 18 publications

Benzodiazepine Alkaloids from Marine‐Derived Endophytic Fungus Aspergillus ochraceus

Benzodiazepine Alkaloids from Marine‐Derived Endophytic Fungus Aspergillus ochraceus

5-Chloroacetyl-4-methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Carboamination and Alkylative Cyclization withCNBond Formation in Stereoselective Syntheses

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