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Friday 4 January 2013

Sulforaphane, a natural product present in cruciferous vegetables like broccoli, reduces childhood leukemia progression


Sulforaphane
1-Isothiocyanato-4-methylsulfinylbutane
Sulforaphane is a molecule, ref1 within the isothiocyanate group of organosulfur compounds. It exhibits anti-cancer and antimicrobial properties in experimental models. It is obtained from cruciferous vegetables such as broccoliBrussels sprouts or cabbages. It is produced when the enzyme myrosinase transforms glucoraphanin, a glucosinolate, into sulforaphane upon damage to the plant (such as from chewing) which allows the two compounds to mix and react. Young sprouts of broccoli and cauliflower are particularly rich in glucoraphanin.
Glucoraphanin.png
glucoraphanin, glucosinolate precursor to sulforaphane
Sulforaphane, discovered by accident in 1995 by a group of scientists researching the anticancer compounds in broccoli, is a phytochemical compound that can be obtained by eating cruciferous vegetables such as arugula, watercress, Brussels sprouts, broccoli, broccoli sprouts, cabbage, cauliflower, bok choy, kale, collards, kohlrabi, mustard, turnip, radish and rutabaga.  Sulforaphane is particularly abundant in watercress and broccoli sprouts.

Sulforaphane, a natural product present in cruciferous vegetables like broccoli, reduces childhood leukemia progression

article
Sulforaphane Induces Cell Cycle Arrest and Apoptosis in Acute Lymphoblastic Leukemia Cells,
K. Suppipat, C. Shik Park, Y. Shen, X. Zhu, H. D. Lacorazza, 
PLOS ONE 2012.
DOI: 10.1371/journal.pone.0051251


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Sulforaphane is a phytochemical belonging to the family of isothiocyanates, which means it contains the typical NCS group.
Sulforaphane was identified in broccoli sprouts, which, of the cruciferous vegetables, have the highest concentration of sulforaphane. It is also found in Brussels sproutscabbage,cauliflowerbok choykalecollardsChinese broccolibroccoli raabkohlrabimustard,turnipradisharugula, and watercress
The optimal level of intake is not known, but some doctors recommend 200 to 400 mcg of sulforaphane daily from broccoli-sprout extracts.
Acute lymphoblastic leukemia is the most common form of blood cancer affecting children. Although the current treatments cure 8 % of the patients, in the remaining cases the disease recurs and it can be fatal. Thus, novel drugs effective against relapses are needed.

To this regard, Koramit Suppipat, Texas Children’s Hospital, USA, and colleagues investigated the anti leukemic properties of sulforaphane, a dietary isothiocyanate abundant in cruciferous vegetables, such as broccoli. This compound blocked the proliferation of pediatric leukemic cells and selectively promoted their death, mostly by inhibiting Akt and mTOR, two serine/threonine kinases necessary for the survival of these malignant cells. When administered orally to mice affected by leukemia, moreover, sulforaphane reduced the progression of the tumor.
This compound may thus be beneficial for acute lymphoblastic leukemia patients at high risk of relapse.
We know that stress accelerates aging and disease.  When you are under stress, your immune system is also compromised, weakening your ability to ward off invading organisms.  Chronic stress raises the level of the excitatory hormones, including norepinephrine and cortisol, which can wear your body down and lead to disease.  Sulforaphane inhibits the norepinephrine-mediated increase in the interleukin-6 levels in the cells, which is a very good thing.  Interleukin-6 is responsible for the shift from acute inflammation to chronic inflammation, the root of so many diseases.  Finding a safe and effective substance that can inhibit the overproduction of norepinephrine, like sulforaphane,  is a significant accomplishment.

Consumption of broccoli sprouts has shown to be potentially effective at inhibitingHelicobacter pylori growth,[2][3] with sulforaphane being at least one of the active agents.[4][2]
Sulforaphane and dietary consumption of cruciferous vegetables are known to affect the action of drug-metabolizing enzymes in vitroand in preliminary human studies.[5] Although no side effects or direct drug interactions have been reported as of 2008, people taking prescription drugs are advised to consult a doctor before taking sulforaphane or broccoli-sprout extracts.
The possible anticancer activity of sulforaphane may be related to the induction of phase-II enzymes of xenobiotic transformation (such as quinone reductase and glutathione S-transferase), and enhancing the transcription of tumor suppressor proteins, possibly via inhibitory effects on histone deacetylase.[6]
Sulforaphane and diindolylmethane (another compound from Brassica vegetables) inhibit cancer growth in vitro and in experimental animals.[7] Sulforaphane downregulated the Wnt/beta-catenin self-renewal pathway in breast cancer stem cells.[7]


Sulforaphane

Sulforaphane

MW: 177
Formula: C6H11NOS2

Linkslinks

  1. Zhang Y, Talalay P, Cho CG, Posner GH (March 1992). "A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure"Proc. Natl. Acad. Sci. U.S.A. 89 (6): 2399–2403. doi:10.1073/pnas.89.6.2399PMC 48665.PMID 1549603.
  2. Yanaka A, Fahey JW, Fukumoto A, Nakayama M, Inoue S, Zhang S, Tauchi M, Suzuki H, Hyodo I, Yamamoto M (April 2009). "Dietary sulforaphane-rich broccoli sprouts reduce colonization and attenuate gastritis in Helicobacter pylori–infected mice and humans". Cancer Prev. Res. 2 (4): 353–360. doi:10.1158/1940-6207.CAPR-08-0192PMID 19349290Lay summary.
  3. Galan MV, Kishan AA, Silverman AL (August 2004). "Oral broccoli sprouts for the treatment of Helicobacter pylori infection: a preliminary report". Dig Dis Sci. 49 (7–8): 1088–1090. doi:10.1023/B:DDAS.0000037792.04787.8aPMID 15387326.
  4. Fahey JW, Haristoy X, Dolan PM et al. (May 2002). "Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors"Proc. Natl. Acad. Sci. U.S.A. 99 (11): 7610–7615.doi:10.1073/pnas.112203099PMC 124299PMID 12032331.
  5. Kall MA, Vang O, Clausen J (March 1997). "Effects of dietary broccoli on human drug metabolising activity". Cancer Lett. 114 (1–2): 169–170. doi:10.1016/S0304-3835(97)04652-1PMID 9103281.
  6. Hayes, JD; Kelleher, MO; Eggleston, IM (2008). "The cancer chemopreventive actions of phytochemicals derived from glucosinolates".European Journal of Nutrition 47 Suppl 2: 73–88. doi:10.1007/s00394-008-2009-8PMID 18458837.
  7. Li et al. (May 2010). "Sulforaphane, a dietary component of broccoli/broccoli sprouts, inhibits breast cancer stem cells"Clinical Cancer Research 16 (9): 2580–2590. doi:10.1158/1078-0432.CCR-09-2937PMC 2862133PMID 20388854.



read about synthesis
[PDF] 

A Facile and Green Synthesis of Sulforaphane

imm.ac.cn/journal/ccl/1709/170905-1152-c060185-p3.pdf
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by D Tong Jian - 2006 - Cited by 3 - Related articles
A Facile and Green Synthesis of Sulforaphane. Tong Jian DING, Ling ZHOU, Xiao Ping CAO*. Sate Key Laboratory of Applied Organic Chemistry and College of ...


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Wednesday 26 December 2012

Iron-Catalyzed Synthesis of 2-Arylbenzo[b]furans




Iron-Catalyzed Synthesis of 2-Arylbenzo[b]furans

Synthetic Communications

Volume 43, Issue 6, 2013


Jianguo YangGuodong Shen & Dingben Chen
pages 837-847

DOI:10.1080/00397911.2011.610550
http://www.tandfonline.com/doi/abs/10.1080/00397911.2011.610550
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Abstract

An iron-catalyzed procedure was employed to achieve both the Sonogashira cross-coupling and intramolecular o-arylation of o-iodophenols and aryl acetylenes/1-substituted-2-trimethylsilyl acetylenes. A variety of 2-arylbenzo[b]furans were synthesized in moderate to good yields under the catalysis of 5% FeCl3 and 10% 1,10-phenanthroline.

Monday 3 December 2012

Sodium dodecyl sulfate in water: greener approach for the synthesis of quinoxaline derivatives





A simple energy efficient one step SDS catalysed 0.03% greener method for the synthesis of quinoxaline der using water as solvent is described

A mild and efficient synthetic method has been developed for the preparation of biologically important quinoxalines in excellent yield from relatively safe precursor Î±-bromoketones and 1,2-diamines using catalytic amount of micellar sodium dodecyl sulfate in water at ambient temperature. The method is also found effective for the introduction of quinoxaline moiety into the ring A of pentacyclic triterpenoid, friedelin. Ambient reaction conditions, renewable catalytic condition, inherently safer chemistry, excellent product yields, and water as a reaction medium display both economic and environmental advantages.

General procedure for quinoxalines

In a typical experimental procedure, o-phenlylenediamine (1 mmol) and Î±-bromoketone (1 mmol) in 1:1 molar ratios was taken in a 50 ml round bottom flask. To this water (3 ml) and 10 mg (0.03 mol%) SDS was admixed. The reaction mixture was then allowed to stir with magnetic spinning bar at room temperature. After the completion of the reaction (checked by TLC), the residue was filtered, washed with water, dried and finally recrystallized from methanol. The desired pure product was characterized by spectral (IR, 1H- and 13C-NMR) data and compared to those reported in literature.

Green Chemistry Letters and Reviews

http://www.tandfonline.com/doi/full/10.1080/17518253.2012.703245

DOI:
10.1080/17518253.2012.703245
Pranab Ghosh & Amitava Mandal
 Department of Chemistry, University of North Bengal, Darjeeling, West Bengal, 734 013, India

Sodium dodecyl sulfate in water: greener approach for the synthesis of quinoxaline derivatives

Quinoxalines are ubiquitous heterocyclic units in pharmaceuticals and bioactive natural products 1–4. They are used as pharmaceuticals and antibiotics such as echinomycin, levomycin, and actinoleutin which are known to inhibit the growth of Gram-positive bacteria and are also active against various transplantable tumors 1–3. Antitumoral properties of quinoxaline compounds have also been investigated


Saturday 24 November 2012

Continuous Flow Synthesis of Organic Electronic Materials – Case Studies in Methodology Translation and Scale-up



 Continuous Flow Synthesis of Organic Electronic Materials – Case Studies in Methodology Translation and Scale-up
 Helga Seyler , Wallace W. H. Wong et al

Australian Journal of Chemistry - http://dx.doi.org/10.1071/CH12406
Submitted: 1 September 2012  Accepted: 3 October 2012   Published online: 19 November 2012
 
Continuous flow chemistry was applied for the derivatization of alkylthiophene building blocks. The advantages of reaction automation and scale-up were demonstrated for selective lithiation-borylation and Knoevenagel condensation of thiophene derivatives. These synthetic approaches allow facile and rapid access to monomer and dyes for organic electronic applications.
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 http://www.publish.csiro.au/paper/CH12406.htm     copy paste link

Wednesday 21 November 2012

Reduction of Sulfonylimines with Raney Nickel




Reduction of Sulfonylimines with Raney Nickel

José Luis García Ruano, José A. Fernández-Salas, M. Carmen Maestro & Alejandro Parra
pages 198-207

  • DOI:10.1080/00397911.2011.594974
  • http://www.tandfonline.com/doi/abs/10.1080/00397911.2011.594974   copy paste link

Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry,Volume 43, Issue 2, 2013  advance article                   

Raney-Ni/EtOH reduction of different N-sulfonylimines provides a new entry for synthesizing sulfonamides in good yields under mild conditions. This protocol, which does not require additional hydrogen, constitutes a cheap, safe, and easy-to-handle alternative procedure to prepare α-branched sulfonamides.

Synthesis of Enantiomerically Enriched α-Bromonitriles from Amino Acids



Synthesis of Enantiomerically Enriched α-Bromonitriles from Amino Acids

Najeh Tka, Jamil Kraïem & Béchir Ben Hassine
pages 735-743, DOI:10.1080/00397911.2011.608142

http://www.tandfonline.com/doi/abs/10.1080/00397911.2011.608142
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Two methods were investigated for the preparation of six chiral α-bromonitriles with different optic purities. The nitrous deamination of amino acids gives α-bromoacids, which react with chlorosulfonyl isocyanate followed by triethylamine to afford α-bromonitriles with moderate enantiomeric excess. However, the dehydration of corresponding α-bromoamids using thionyl chloride gives α-bromonitriles with good enantiomeric excess up to 94%. The use of phosphoryl chloride instead of thionyl chloride results in more than 30% racemization as determined by high-performance liquid chromatograpic analysis.

Sunday 18 November 2012

Synthesis of Quinolines Using Nano-Flake ZnO as a New Catalyst under Solvent-Free Conditions

J. Iran. Chem. Soc., Vol. 8, No. Suppl., February 2011, pp. S119-S128.
http://www.ics-ir.org/jics/archive/v8/S1/Articles/pdf/JICS-8-S1-Article-13.pdf
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Synthesis of Quinolines Using Nano-Flake ZnO as a New Catalyst under Solvent-Free Conditions


M. Hosseini-Sarvari, Department of Chemistry, College of Science, Shiraz University, Shiraz, 71454, Iran

     Catalytic activity of nano-flake ZnO for synthesis of quinoline derivatives and their related polyheterocycles under solvent-free conditions has been studied. Nano-flake ZnO has been successfully synthesized by conventional heating of a solution approach using ZnOAc.2H2O and Urea. This method is simple, cost-effective, and environmentally benign and the catalyst can be reused for several times.