Efficient one-pot synthesis of anti HIV and antitumor compounds: harman and substituted harmans

Kusurkar, Radhika S.; Goswami, Shailesh K.; Vyas, Sandhya M.

doi:10.1016/s0040-4039(03)01046-3

Cited by 42 publications

(11 citation statements)

References 13 publications

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“…The carbazole framework represents an important structural constituent in numerousn atural productsa nd synthetic compounds that display aw ide variety of biological and pharmaceuticala ctivities. [1,2] In addition, carbazoles also playavital role as potentialb uilding blocks for hole-transporting [3] and photorefractive materials, [4] as well as organic dyesf or solar cells. [5] As ar esult,t he synthesis of carbazole derivatives has attracted much attention, [1c, 6] and various strategies have been developed involving direct arylation reactions, [7] CÀNb ond formation of biaryl amines or azides, [8] benzannulation reactions, [9] and other methods.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Sequential Propargylation/Cycloisomerization: A Facile [4+2]‐Benzannulation Approach to Carbazoles

Reddy

Valleti

Dilipkumar

2016

Chemistry A European J

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A novel one-pot [4+2]-benzannulation approach to substituted carbazoles is accomplished by acid-catalyzed C3-propargylation of 2-alkenyl/aryl indoles with 1-aryl propargylic alcohols, followed by cycloisomerization. A variety of 2-alkenylated indoles and 2-aryl/heteroaryl indoles successfully participated in this tandem reaction with 1-aryl/heteroaryl propargylic alcohols to provide diversely substituted and annulated carbazoles, as well as an aza[5]helicene.

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Section: Introductionmentioning

confidence: 99%

One‐Pot Sequential Propargylation/Cycloisomerization: A Facile [4+2]‐Benzannulation Approach to Carbazoles

Reddy

Valleti

Dilipkumar

2016

Chemistry A European J

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“…Some procedures utilise the suitable phosphorane and indole-3-carbaldehydes, 28 or the gramine framework coupled with aldehydes. 29 The Heck coupling has also been exploited. [30][31][32][33][34] Since the proposed procedures resort to the indole scaffold as a starting reagent, their applicability to the synthesis of variously substituted targets is limited, as few functionalised indoles are commercially available.…”

Section: Introductionmentioning

confidence: 99%

Heck reaction on protected 3-alkyl-1,2-dien-1-ols: an approach to substituted 3-alkenylindoles, 2-alkoxy-3-alkylidene-2,3-dihydrobenzofuranes and -indolidines

et al. 2010

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A phosphine-free annulation reaction has been exploited for the preparation of substituted 3-alkenylindoles, 2-alkoxy-3-alkylidene-2,3-dihydrobenzofuranes and -indolidines in good to excellent yields. This has been done by reaction of protected 3-alkyl-1,2-dienols with o-iodophenols or protected o-iodoanilines. Two different heterocyclic skeletons were obtained, depending on the electron-donating properties of the heteroatom involved in the annulation process.

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“…10) In our program to develop CDK2 inhibitors, we recently investigate the β-carboline alkaloids containing a planar tricyclic system as a large group of naturally-occurring and synthetic alkaloids, [11][12][13][14] which has a broad spectrum of biochemical effects and pharmaceutical properties. These compounds have been shown to intercalate into DNA, to inhibit CDK, topisomerase and monoamine oxidase, and to interact with benzodiazepine receptors (BZ), 5-hydroxy serotonin receptors (5-HT), dopamine (DA) and imidazoline receptors.…”

Section: )mentioning

confidence: 99%

Synthesis and Structure of the β-Carboline Derivatives and Their Binding Intensity with Cyclin-Dependent Kinase 2

Wang

Jin

Lin

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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Series of 3-substituted of 6-aminosulfonyl-β-carbolines were designed and synthesized. In addition, the binding mode of these β-carboline derivatives with cyclin-dependent kinase 2 (CDK2) was studied by means of fluorescence measurements and molecular docking calculation. The results showed that replacement of 3-cyclohexylmethoxy group will increase the hydrophobic binding interaction with the deep hydrophobic pocket of CDK2 correlate to the higher binding intensity.Key words cyclin-dependent kinase 2; β-carboline; synthesis; molecular docking; fluorescence It is well known that the phases of the cell cycle are driven by cyclin-dependent kinases (CDKs). Upon complexation with its activating proteins, cyclin E or cyclin A, cyclin-dependent kinase 2 (CDK2) modulates the activity of many cellular substrates via phosphorylation on serine (Ser) and/or threonine (Thr) residues.1-4) Abnormal CDK control of the cell cycle has been strongly linked to the molecular pathology of cancer. 5)The importance of CDK2 for cell cycle progression has led to an active pursuit of small molecule inhibitors of this enzyme as a possible treatment against cancer and other hyper-proliferative disorders.6-9) All CDK inhibitors, identified so far, function by competing with ATP for binding to the catalytic site. Actually several CDK inhibitors have entered clinical evaluation for the treatment of cancer, including flavopiridol, amino-thiazole compound.10) In our program to develop CDK2 inhibitors, we recently investigate the β-carboline alkaloids containing a planar tricyclic system as a large group of naturally-occurring and synthetic alkaloids, [11][12][13][14] which has a broad spectrum of biochemical effects and pharmaceutical properties. These compounds have been shown to intercalate into DNA, to inhibit CDK, topisomerase and monoamine oxidase, and to interact with benzodiazepine receptors (BZ), 5-hydroxy serotonin receptors (5-HT), dopamine (DA) and imidazoline receptors. [15][16][17][18][19][20][21][22][23] Inspired by these results, our research group recently focused on first of all, using a structure-guided strategy based on CDK2 as appropriate means to generate potent CDK2 inhibitors; then to synthesize disubstituted β-carbolines and to complete their biological evaluation study. As a part of our systematic work, in this paper, structure modification of β-carboline based on increasing its hydrophobic nature has been adopted. Herein we reported the design and synthesis of series of 3-substituted of 6-aminosulfonyl-β-carbolines. Series of 3-substituted compounds with different hydrophobic groups (Chart 1) were synthesized and one of their structures was elucidated with X-ray crystal analysis. The new derivatives were prepared following the reaction sequences depicted in Charts 2-4. Their binding intensity with CDK2 was measured by fluorescence spectroscopy. ExperimentalSynthesis The target compounds were prepared using the reaction sequence. All the chemical structures of the synthesized compounds were confirmed by spectroscopic me...

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Efficient one-pot synthesis of anti HIV and antitumor compounds: harman and substituted harmans

Cited by 42 publications

References 13 publications

One‐Pot Sequential Propargylation/Cycloisomerization: A Facile [4+2]‐Benzannulation Approach to Carbazoles

One‐Pot Sequential Propargylation/Cycloisomerization: A Facile [4+2]‐Benzannulation Approach to Carbazoles

Heck reaction on protected 3-alkyl-1,2-dien-1-ols: an approach to substituted 3-alkenylindoles, 2-alkoxy-3-alkylidene-2,3-dihydrobenzofuranes and -indolidines

Synthesis and Structure of the β-Carboline Derivatives and Their Binding Intensity with Cyclin-Dependent Kinase 2

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