Synthesis of Thienodolin

Engqvist, Robert; Javaid, Atif; Bergman, Jan

doi:10.1002/ejoc.200400073

Cited by 42 publications

(23 citation statements)

References 14 publications

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“…The mixture was cooled, poured into ice water and basified with 30% NH 4 OH 32. The aldehyde 2d was collected by filtration with a yield of 30%: mp 180–190°C dec.…”

Section: Methodsmentioning

confidence: 99%

Substituted E-3-(3-Indolylmethylene)-1,3-dihydroindol-2-ones with Antitumor Activity. In Depth Study of the Effect on Growth of Breast Cancer Cells

et al. 2010

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The synthesis of new substituted E-3-(3-indolylmethylene)1,3-dihydroindol-2-ones is reported. The antitumor activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. Structure-activity relationships are discussed. The action of selected compounds was investigated in MCF-7 breast cancer cells. The ability of these derivatives to inhibit cellular proliferation was accompanied by increased level of p53 and its transcriptional targets p21 and Bax, interference in the cell cycle progression with cell accumulation in the G2/M phase, and lastly activation of apoptosis.

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“…The mixture was cooled, poured into ice water and basified with 30% NH 4 OH 32. The aldehyde 2d was collected by filtration with a yield of 30%: mp 180–190°C dec.…”

Section: Methodsmentioning

confidence: 99%

Substituted E-3-(3-Indolylmethylene)-1,3-dihydroindol-2-ones with Antitumor Activity. In Depth Study of the Effect on Growth of Breast Cancer Cells

et al. 2010

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“…[4] The total chemical synthesis was accomplished in three steps starting from 6-chlorooxindole. [5] Thienodolin was the first actinomycete metabolite to show concentration-dependent growth-regulating activity in rice seedlings.G rowth was promoteda tl ow concentrations ( 1.2-12 mm), but inhibited at higherc oncentrations (> 40 mm). [4] It is of significant pharmaceutical interest, because recently it was demonstrated that thienodolin exhibits anti-inflammatory and anti-tumor activity through suppression of nitric oxide synthases.…”

Section: Introductionmentioning

confidence: 99%

Characterization of the Aminotransferase ThdN from Thienodolin Biosynthesis in Streptomyces albogriseolus

2016

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In Streptomyces albogriseolus the indolethiophen alkaloid thienodolin is derived from tryptophan. The first step in thienodolin biosynthesis is the regioselective chlorination of tryptophan in the 6-position of the indole ring. The second step is catalyzed by the aminotransferase ThdN. ThdN shows sequence homology (up to 69 % similarity) with known pyridoxal 5'-phosphate-dependent aminotransferases of the aspartate aminotransferase family from Gram-positive bacteria. thdN was heterologously expressed in Pseudomonas fluorescens, and the enzyme was purified by nickel-affinity chromatography. ThdN is a homodimeric enzyme with a mass of 90 600 kDa and catalyzes the conversion of l-tryptophan and a number of chlorinated and brominated l-tryptophans. The lowest K values were found for 6-bromo- and 6-chlorotryptophan (40 and 66 μm, respectively). For l-tryptophan it was 454 μm, which explains why thienodolin is the major product and dechlorothienodolin is only a minor component. The turnover number (k ) for 7-chlorotryptophan (128 min ) was higher than that for the natural substrate 6-chlorotryptophan (88 min ).

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“…In the course of our ongoing studies of the chemical and biological properties of linear hetero[b]fused indoles [1][2][3][4], we have developed effective and simple methods for the synthesis of pharmacologically interesting pyridazino [4,3b]indoles [5], pyrano [3,2-b]indoles [6], pyrrolo [3,2-b] indoles [7], imidazo [4,5-b]indoles, thiazolo [5,4-b]indoles [8], and some of their analogs [9,10]. A number of representatives of these series displayed antituberculosis, monoamine oxidase inhibiting, antiviral, antihypoxic, and hepatoprotective activities some of which may be attributable to monoamine oxidase inhibition.…”

Section: Introductionmentioning

confidence: 99%

A Versatile Approach for the Synthesis of 8H‐Thieno[2,3‐b]indoles and N‐[2‐(2‐N‐(R₁,R₂)‐2‐Thioxoacetyl)‐phenyl]acetamides from 1‐Acetyl‐1,2‐dihydro‐3H‐indol‐3‐one (Acetylindoxyl) and Its Derivatives: A Novel Synthesis of Intermediate (1‐Acetyl‐1H‐indol‐3‐yl)malononitrile/cyanoacetates

Velezheva

Lepyoshkin

Turchin

et al. 2013

Journal of Heterocyclic Chem

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We report on two approaches for the synthesis of new 2‐amino‐3‐cyano/alkoxycarbonyl‐8H‐thieno[2,3‐b]indoles 5 and another one for the synthesis of 2‐N,N‐dialkylamino‐3‐cyano/aryl‐8H‐thieno[2,3‐b]indoles 16, based either on acetylindoxyl 1 and (1‐acetyl‐1H‐indol‐3‐yl)malononitrile/cyanoacetates 14 or 2‐bromoacetylindoxyl 2 transformations. A new, simple, rapid, and efficient method for the synthesis of valuable key intermediate malononitrile/cyanoacetates 14 based on acetylindoxyl 1 condensation with malononitrile or cyanoacetates in the presence of triethylamine has been developed. A number of synthetic procedures for the preparation of thioacetamides 6, 1‐acetylthioisatin 8, and 2,2‐disubstituted indoxyls 13 have been elaborated during the synthesis of thieno[2,3‐b]indoles. Thioacetamides 6 have been shown as novel agents active against Mycobacterium tuberculosis H37Rv, the cause of tuberculosis, with minimal inhibitory concentration values ranging between 5 and 21 μg/mL.

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Synthesis of Thienodolin

Cited by 42 publications

References 14 publications

Substituted E-3-(3-Indolylmethylene)-1,3-dihydroindol-2-ones with Antitumor Activity. In Depth Study of the Effect on Growth of Breast Cancer Cells

Substituted E-3-(3-Indolylmethylene)-1,3-dihydroindol-2-ones with Antitumor Activity. In Depth Study of the Effect on Growth of Breast Cancer Cells

Characterization of the Aminotransferase ThdN from Thienodolin Biosynthesis in Streptomyces albogriseolus

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