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indole

در نشریات گروه شیمی
تکرار جستجوی کلیدواژه indole در نشریات گروه علوم پایه
  • Teeba Khalid Adnan, Khansa Yousif Ahmed, Areej Ali Jarullah*

    In this research article, the Schiff base ligand 3-((2-amino-4-nitrophenyl) imino) indolin-2-one(Ln) was synthesized through the reaction between indoline 2, 3-dione and 4-nitrobenzene-1,2-diamine. The synthesized ligand was then characterized using various analytical techniques,including1HNMR, UV-Vis, FT-IR, and element analysis C.H.N. The presence of nitrogen (N) andoxygen (O) atoms in the ligand structure makes it suitable for coordination chemistry. Furthermore,the ligand was employed for the synthesis of metal ion complexes by reacting it with transitionmetal salts such as CoCl2.6H2O, NiCl2.6H2O, CuCl2.2H2O, and anhydrous ZnCl2. These metal(II) complexes were subsequently utilized for the oxidation of alcohols in toluene under thermalconditions. To further investigate the properties of the newly prepared complexes [M(Lnn)2]Cl2,various characterization techniques, including FTIR, UV-Vis, magnetic susceptibility, atomicabsorption spectroscopy, and molar conductance were employed. Moreover, this study aimed toevaluate the impact of the synthesized ligand and its complexes on the Mitotic Index in humanlymphocyte cells. A concentration of 100μg/mL was utilized, and the exposure time was set at 15minutes. The results indicated that the ligand had a greater effect on the rate of lymphocyte celldivision compared to the complexes. This suggests that the ligand exhibited a stronger resemblanceto colchicine in terms of inhibiting lymphocyte division during the equatorial phase.

    Keywords: Complexes, Indole, Isatin, Lymphocyte Cells Of Humans, Oxidation
  • Farzaneh Yazdan Kushkoo, Hojatollah Khabazzadeh *, Moj Khaleghi
    A new series of 1,3,4-oxadizole-containing azo derivatives were synthesized in this research. The structural properties of the newly-synthesized compounds were assessed by IR and 1H- and 13C-NMR spectroscopic techniques. The antibacterial properties of the synthesized azo compounds were evaluated against Gram-negative and Gram-positive bacteria in vitro, revealing broader antibacterial spectrum on both bacteria groups for derivatives containing indole ring. In particular, most compounds had antibacterial effects on Staphylococcus aureus (ATCC 25923), while Pseudomonas aeruginosa (ATCC 27853) exhibited resistance against all azo compounds.
    Keywords: Oxadiazole, Indole, Salicylic Acid, Pyrazole, Antibacterial
  • حسن حذرخانی*

    در این پژوهش، تاثیر کمپلکس کبالت تری گوانیدین بنزایمیدازول تریس(تتراکیس (5،3- تری فلویورومتیل) فنیل) بورات بر روی واکنش الکترون دوستی آروماتیکی ایندول بررسی شده است. این واکنش به دلیل تشکیل پیوند کربن - کربن و شرکت یک ترکیب هتروسیکل از این نظر اهمیت دارد که می تواند در سنتز ترکیب های هتروسیکل راهگشا باشد. برای این منظور ابتدا کمپلکس کبالت تری گوانیدین بنزایمیدازول تری کلرید Co(GBI)33+, 3Cl- از واکنش کبالت (II) کلرید شش آبه با گوانیدین بنزایمیدازول سنتز شده و تاثیر آن بر واکنش جایگزینی - افزایشی الکترون دوستی آروماتیکی مطالعه شد. نتیجه ها نشان دادند که این کمپلکس نمی تواند واکنش ایندول را با بتا- نیترو استایرن کاتالیز کند. سپس کمپلکس کبالت تری گوانیدین بنزایمیدازول تریس (تتراکیس (5،3- تری فلویورومتیل) فنیل) بورات، Co (GBI) 33+, 3BArf-  سنتز شده و واکنش الکترون دوستی ایندول با بتا- نیترواستایرن در حضور مقدار 10% مولی از این کمپلکس مورد مطالعه قرار گرفت. نتیجه ها نشان دادند که جایگزینی یون کلرید با یون تتراکیس (5،3- تری فلویورومتیل) فنیل) بورات سبب می شود که واکنش به خوبی پیش برود و کاتالیز شود زیرا خصلت چربی دوستی کمپلکس افزایش یافته و در حلال های با قطبیت کم تر مانند دی کلرومتان حل می شود و در مجاورت بتا- نیترواستایرن قرار گرفته و با آن برهمکنش های قوی تری می دهد. به طوری که بخش گوانیدین بنزایمیدازول موجود در کمپلکس، با بتا- نیترواستایرن پیوند هیدروژنی می دهد وآن را برای حمله ایندول واکنش پذیرتر می کند. در ادامه واکنش 5- متوکسی ایندول نیز با بتا- نیترواستایرن بررسی گردید و مشخص شد که این کمپلکس به طور کلی واکنش الکترون دوستی ایندول و ایندول های استخلافی با بتا -نیترو استایرن را سرعت می بخشد.

    کلید واژگان: گوانیدین بنزایمیدازول، ایندول، جایگزینی الکترون دوستی آروماتیکی، بتا- نیترواستایرن، کمپلکس کبالت
    Hassan Hazarkhani *

    The addition of aromatic substrates to electron-deficient alkenes, which in many respects may be considered a Friedel– Crafts type alkylation, is a key reaction in synthetic organic chemistry for the formation of new C-C bonds. Indole and many of its derivatives are relevant units in many naturally occurring compounds, because of their pharmacological and biological properties. Due to the increased nucleophilic reactivity of C3 position of indole ring, it is often used for the subsequent transformations leading to different indole alkaloids. Here I report an efficient catalyst that can catalyzes the electrophilic substitution of indole with electron deficient alkenes. First, Cobalt tris(2-guanidinobenzimidazole), tri chloride (Co(GBI)33+, 3Cl-)  is prepared and then the reaction of indole with beta - nitrostyrene has studied. No product was detected, so the reaction conditions such as the solvents and the amount of catalyst were changed, but the results were the same. After that the chloride moiety of the complex were replaced with tetrakis[(3,5-trifluoromethyl)phenyl]borate (Barf-)anion and the reaction has run on different condition. Our results showed that Cobalt tri(2-guanidinobenzimidazole), tetrakis[(3,5-trifluoromethyl)phenyl]borate (Co(GBI)33+, 3BArf- ) catalyzes the reaction of indole with β - nitrostyrene and afforded the product in high yields. It is noteworthy to mention that using lipophilic anions such as BArf- [(B(3,5-C6H3(CF3)2)4-] , the catalyst could be solubilized in nonpolar solvents that do not compete with substrates for the hydrogen bonding sites.

    Keywords: aromatic electrophilic substitution, Co (III) complex, Indole, β- Nitrostyrene, guanidinobenzimidazole
  • Noor Ud Din Zargar*, Khaliq Uz Zaman Khan

    The field of heterocyclic chemistry is vast and has played a significant role in synthetic organic chemistry. Heterocyclic compounds and methods for their synthesis form the bedrock of modern medicinal and pharmaceutical research. Indoles and Oxindoles are the most studied bicyclic nitrogen heterocycles. The selective acylation of indoles often requires sensitive and reactive acyl chloride derivatives. A chemoselective N-acylation of indoles1 using thioesters 2 as a stable acyl source has been reported. Interaction of 1-acylindoles 10 with acetyl chloride in the presence of AlCl3 yields the corresponding 1- acyl-3-acetylindoles 11 which upon hydrolysis affords 3-acetylindole12.Addition of (1Hindol- 3-yl) magnesium iodide (16) to 2-(benzyloxy) acetyl chloride 17 in diethyl ether forms 3-benzyloxyacetylindole 18. Acylation of Oxindole 20 with chloroacetyl chloride affords 5- chloromethyl ketone derivatives31whichwhen treated with thioureas and thioamides leads to the formation of 5-thiazole oxindoles32.This article focuses on various synthetic methods and suggested mechanism of different indole and oxindole derivatives.Apart from this, applications of medicinal importance of these heteroatom compounds have also been discussed.

    Keywords: Acylation, Indole, Oxindole, Heterocycles, Synthesis, Mechanism
  • Auhood Kadhim Zaid *
    The present study includes the synthesis and characterization of thiazolidinedion containing indole ring. Two compounds were prepared: (4-fluorophenyl)-2-(1H-indol-3-yl)thiazolidin-4-one (I) and(4-( dimethylamino)phenyl)-2-(1H-indol-3-yl)thiazolidin-4-one(II), the prepared compounds  diagnosed by using infrared spectra, NMR spectra (1H-NMR), and the results were identical to what is expected in practice. The Gaussian program was used for the computational study of thiazolidinedion and the theoretical calculations of the thermodynamic variables showed that compound (I) is the more softness with the lowest hardness. Meanwhile, compound (II) the more hardness with less softness.
    Keywords: thiazolidinone, heterocyclic derivatives, Indole, Gaussian program
  • Mohammad Bakherad *, Ali Keivanloo, Narges Rahmani, Leila Kamrani

    A series of novel 1,2,3-triazoles-linked indole derivatives were prepared by the reaction of 2-aryl-1-(prop-2-ynyl)-1H-indole-3-carbaldehydes with aryl azides via copper-catalyzed azide-alkyne cycloaddition reactions in the presence of sodium ascorbate, as a reducing agent. The effects of catalysts, solvents, and reaction temperature were investigated. Under the optimal condition, 1,2,3-triazoles linked-indoles were obtained in 63–92% yields.

    Keywords: Indole, Triazole, Aryl azide, Propargyl bromide
  • مهدی پردل*، صادق علامه، محمود ابراهیمی

    در این کار پژوهشی، با توجه به اهمیت بسیار زیاد کرون اترها در شیمی کمپلکس ها و نیز در زمینه علوم فارماکولوژی، روشی جدید برای تهیه چندین کرون هتروسیکل بر پایه ایندول با استفاده از کاتالیزگر تیتانیوم نانو اکسید ابداع شد. برای این منظور نخست از واکنش 2- متیل ایندول با تری اتیلن گلیکول توسیله شده، در حلال DMF و شرایط بازی KOH، ترکیب 2-متیل-1-(2-(2-(2-(2-متیل-H1-1-ایندول)اتوکسی)اتوکسی)اتیل)-H1-ایندول با بازده مناسب به دست آمد. پس از تعیین شرایط بهینه برای تهیه کرون اترها (دمای محیط، حلال دی کلرومتان و نسبت کاتالیزگری % 5 مولی)، مشتق های کرونی موردنظر از واکنش ترکیب 2-متیل-1-(2-(2-(2-(2-متیل-H1-1-ایندول) اتوکسی)اتوکسی)اتیل)-H1-ایندول با مشتق های متفاوت آلدهیدی تهیه شدند. از جمله برتری های این روش می توان به بازده بالا، غیر سمی بودن کاتالیزگر و استفاده دوباره از آن اشاره کرد.

    کلید واژگان: کرون اتر، ایندول، کاتالیزگر، تیتانیوم نانوذره های اکسید
    Mehdi Pordel *, Sadegh Allameh, Mahmood Ebrahimi

    In this research, due to the high importance of crown ethers in complexometric and also in the field of pharmacology, a new method for the preparation of several heterocyclic crowns ethers was proposed using titanium nano-oxide catalysts. To this end, the reaction of 2-methyl-indole with tosylated triethylene glycol, led to the formation of 2-methyl-1- (2- (2- (2- (2-methyl-H1-1 -indole (ethoxy) (ethoxy) ethyl) -1H-indole in DMF solvent and the KOH. After determining the optimum conditions for the preparation of the crowns (room temperature, dichloromethane solvent and the catalytic ratio of 5 mol%), the chronological derivatives of the crown ethers were obtained from the reaction of the 2-methyl-1- (2- (2- (2- (2-methyl-H1-1 -indole (ethoxy) (ethoxy) ethyl) -1H-indole with different derivatives of aldehydes. One of the advantages of this method is the high efficiency, non-toxicity of the catalyst, and its reuse.

    Keywords: Crown Ethers, Indole, Catalyzer, Nano TiO2
  • Kaveh Hemmat, Mohammad Ali Nasseri *, Ali Allahresani
    The preparation, characterization, and immobilization of cobalt (III) salen complex on CoFe2O4@SiO2 nanoparticle (CoFe2O4@SiO2@ Co(III) salen complex) are described. Co(III) salen complex loaded on ferrite cobalt-silica nanoparticle is characterized by TEM, SEM-EDX, VSM and FT-IR analyses. The efficiency of CoFe2O4@SiO2@Co(III) salen complex as a catalyst was carried out in the 3-indolylation reaction of indole with isatin derivatives in the water at 80 . Di-indolyloxindole was achieved with excellent yield (95%), using indole, isatin, and CoFe2O4@SiO2@Co(III) salen complex within 2 h in water as solvent at 80 . Moreover, the recoverability and reusability of CoFe2O4@SiO2@Co(III) salen complex were investigated.
    Keywords: Co(III) salen complex, Di-indolyloxindole, indole, Cobalt ferrite, Isatin, Multicomponent
  • MohammadHosein Nasirtabrizi *, Hamideh Khosroshahi

    Synthesis of some novel indole derivatives has been undertaken by the reaction of poly(maleic anhydride-co-styrene), P(MA-co-St), poly(maleic anhydride-co-chloromethyl styrene), P(MA-co-CMS), poly (maleic anhydride-co-methyl methacrylate), P(MA-co-MMAc) and poly(maleic anhydride-co-methacrylate) P(MA–co–MAc), copolymers with indole in the presence of NaH at -5ºC. Compositions of the copolymers were obtained using related 1H NMR spectra and the polydispersity indices of the copolymers determined using gel permeation chromatography (GPC). The anhydride group possesses a higher reactivity with the indole group. The ring opening reaction between the anhydride group and the indole is simple and fast. All the resulted polymers were characterized by FT-IR and 1H NMR spectroscopic techniques. The glass transition temperature (Tg) of all the copolymers was determined by dynamic mechanical thermal analysis (DMTA). All the polymers containing indole groups showed a high glass transition temperature in comparison with the unmodified copolymers (I-IV). It was found that these polymers with indole moieties have high thermal stability and the presence of bulky indole groups in polymer side chains leads to an increase in the rigidity of polymers.

    Keywords: Chemical modification, Maleic anhydride, Indole, dynamic mechanical thermal analysis (DMTA), glass transition temperature
  • Manickam Sathiyaraj *, PERUMAL VENKATESH
    The ultrasound assisted preparation of 1-benzyl-1-indole (arylation) from the reaction of benzyl chloride (BC) and indole was carried out successfully using solid sodium hydroxide and catalyzed by multi-site phase-transfer catalyst (MPTC) viz., 1,4-benzyl-1,4-diazoniab-icyclo[2.2.2]octanium dichloride in a solid–liquid reaction condition (SL-PTC). Water was introduced in a trace quantity to the reaction system to avoid a serious hydration of active intermediate. The potentiality of the multi–site phase-transfer catalyst was demonstrated by following the kinetics arylation of indole under pseudo–first order conditions by employing aqueous sodium hydroxide and indole in excess. The reaction was monitored by gas Chromatography. The synthesized MPTC and 1-benzyl-1-indole were characterized by 1H NMR and 13C NMR. The reaction is greatly enhanced in the solid–liquid system, catalyzed by multi-site quaternary ammonium salt (MPTC) and ultrasound irradiation (28 kHz, 300W) in a batch reactor.
    Keywords: Ultrasound, Interfacial reactions, Indole, Kinetics, Benzyl chloride
  • Majid Momahed Heravi, Hoda Hamidi *, Narges Karimi, Akram Amouchi
    An efficient and facile procedure has been developed for the ring opening of epoxides with nitrogen heterocycles such as indole and imidazole in the presence of Caro's acid-silica gel (CA-SiO2) as catalyst in solventless system. The reactions were administered underneath Solvent-free conditions. The current methodology offers many benefits like good yields, easy procedure, simple work-up and ecofriendly reaction condition. The catalyst is well ready, stable and economical underneath the reaction conditions.
    Keywords: Regioselectivity, Indole, Imidazole, Epoxide, Caro's acid-silica gel
  • Ajaz Dar, Atul Dwivedi, Parameswar Iyer, Abu Khan *
    The newly synthesized 3-(phenyl(phenylthio)methyl)-1H-indole ligand demonstrates chemosensor activity towards environmental and clinically important metal ions viz. Hg2+ and Cu2+, via fluorescence intensity enhancement. The rigid complex ceases non-radiative channels with respect to the free ligand. Incorporation of water and significant fluorescence enhancement in presence of interfering metal ions make the method superior over others and detect trace amount of metal ions into the aqueous based medium. Also, the detection of Hg2+ and Cu2+ ions are considered as subjects of an increasing societal demand as well as responsible for neurodegenerative disorders.
    Keywords: Chemosensor, Hg2+ ion, Cu2+ ion, Fluorescence, Electron transfer, Indole
  • Vishvanath D. Patil *, Amruta Salve, Vaishnav D. Gharat, Nilesh Gawand

    There is need to develop simple, efficient & economically viable chemical pathways to synthesise biologically active & commercially important heterocyclic Bis(indolyl) methanes1.The indole ring is an important constituent of many natural products, pharmaceuticals & other compounds of commercial importantance2. The literature survey shows that Bis(indolyl) methanes are known to increase estrogen metabolism in human beings and hence can be used for the treatment of breast cancer, also it exhibits antibacterial activities3,4,5. This wide range of  applications has leaded the chemists to develop new methods to synthesise Bis (Indolyl) methanes. Various methods have been developed for their synthesis using Lewis acid catalysts6-12, ionicliquids13, trichloro-1,3,5-triazine14, and potassium hydrogen sulphate15.However, many of these reported methods suffer from one or other disadvantages such as harsh reaction conditions and reagents that are expensive, moisture sensitive. A mild and efficient catalyst for the synthesis of bis(indolyl) methanes is highly desirable.

    Keywords: Bis(indolyl) methanes, CeO2 nanoparticles, carbonyl compounds, indole, Aldehydes
  • Sami Sajjadifar *, Ghobad Mansouri, Shefa Miraninezhad

    Silica supported-boron sulfonic acid (SBSA) was used as a cheap and mild bronsted acidic in the reaction of indole with aldehydes to afford the corresponding bis(indolyl)methanesin in solvent free grinding and room temperature. The catalyst is also effective in the reaction in good yields. This methodology offers several advantages, such as good yields, reusability of catalyst, short reaction times, simple procedure, and mild conditions. The catalyst can be recovered and reused without loss of activity. The work-up of the reaction consists of a simple filtration, followed by concentration of the crude product and purification.

    Keywords: Indole, Bis(indolyl)methane, Boron Sulfonic Acid, Aldehyde, Synthesis
  • Ali Allahresani *
    In this study, novel CuO/g-C3N4 nanocomposite was simply synthesized by impregnation of g-C3N4 with CuO nanoparticles. Then, the heterogeneous catalyst was characterized by various techniques including Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA) and transmission electron microscopy (TEM). Moreover, the Friedel–Crafts 3-indolylation reaction of isatin with indole derivatives in water as a green solvent was investigated using catalytic amount of CuO/g-C3N4 nanocomposite. The results showed that di-indolyloxindole derivatives are synthesized in good to excellent yields at mild conditions. Finally, this method has some advantages including the use of water as a green solvent, short reaction time, room temperature, easy work up and excellent yields.
    Keywords: CuO-g-C3N4 nanocomposite, di-indolyloxindols, indole, isatin
  • Gohani M., H. Van Tonder J., C.B. Benzuidenhoudt B.*
    Although several methods for the preparation of 4o propargyl indole derivatives have been published, this synthetic transformation is complicated by the tendency of 3o propargyl alcohols to form allenium intermediates in acidic media. It is therefore a challenge to find an efficient method for the C-3 propargylation of indoles with 3° propargylic alcohols. In this paper we wish to report on the successful application of silica gel impregnated with NaHSO4 as catalyst for the preparation of 4o propargyl indole derivatives.
    Keywords: Alkylation, Catalyst, Indole, Propargylic alcohols, Sodium bisulfate, silica
  • Zahra Lasemi, Bahareh Sadeghi, Fereshteh Amiri Tavasoli
    Nano silica sulfuric acid as a solid acid, was described to be an effective catalyst for one-pot three-component reaction of kojic acid, aryl aldehydes and indoles for the preparation of 2-substituted aryl (indolyl) kojic acid derivatives. The catalyst was prepared by combination of chlorosulfonic acid to nano silica gel. The size of nanoparticles were observed with SEM.All prepared compounds with melting points, 1H NMR and 13C NMR were characterized. High yields, simple operation, easy-work procedure, mild reaction conditions are some advantages of this protocol. The present method does not involve any hazardous organic solvent. Therefore, this procedure could be classified as green chemistry.
    Keywords: Kojic acid, Indole, Nano silica sulfuric acid, Aldehyde, Multi, component
  • Kobra Nikoofar
    Ammonium monovanadate (NH4VO3) has been devoted as an efficient, commercially available, eco-friendly and reusable catalyst for the synthesis of bis(indolyl)methanes (BIMs), oxindole derivatives and also Michael adducts of indoles at 50 °C under solvent-free conditions. The reusability of this solid acid catalyst in addition with its selectivity has also been examined.
    Keywords: Indole, Isatin, α β, Unsaturated compounds, Alkylation, Ammonium monovanadate
  • باقر افتخاری سیس
    سیستم D–π–A جدیدی دارای ساختار 3-هیدروکسی ایندول طی چهار مرحله سنتز شده است، که خواص سولواتوکرومیسم جالبی نشان می دهد، بطوریکه در کلروفرم، زرد رنگ بوده، در DMF، قرمز، در استون، بنفش، در DMSO، ارغوانی تیره و در استونیتریل، سبز رنگ می باشد. همچنین مطالعات فلوئورسانسی رنگینه حاصل نشان داده است که طول موج نشری وابسته به قطبیت حلال می باشد. محاسبات شیمی کوانتومی که با نرم افزار گوسین 3 تحت تراز B3LYP/6-31G* انجام شده است، نشان داده است که اوربیتال هومو روی قسمت الکترون دهنده 3-هیدروکسی ایندول و لومو روی قسمت الکترون گیرنده متیلیدن مالونونیتریل توزیع شده است.
    کلید واژگان: D- π- A، ایندول، سولواتوکرومیسم، محاسبات DFT
    Bagher Eftekhari-Sis
    A novel D–π–A system having indole moiety 5 was synthesized in four steps، which exhibit interesting solvatochromism ranging from yellow in CHCl3 to red in DMF، violet in acetone، deep purple in DMSO and green in CH3CN. Also the studies on the fluorescence properties of 5 in different solvents revealed that the emission peaks are dependent on the polarity of solvents. The quantum–chemical calculations of 5 was performed using the Gaussian 03 program at the B3LYP/6-31G* level، which revealed that the HOMO is localized on the 3-hydroxy indole donor moiety، while LUMO is localized on the methylidene dimalononitrile acceptor moieties.
    Keywords: Donor–π–acceptor, Indole, Solvatochromism, DFT calculations
  • Somnath S. Gholap, Umesh P. Deshmukh, Macchindra S. Tambe
    An efficient synthesis of some novel coumarin derivatives via 1, 4- Michael addition of indole to coumarin chalcones catalyzed by cellulose sulphonic acid (CSA) under solvent free conditions is described. The corresponding Michael addition products were obtained in good to excellent yield. The synthesized compounds were screened for their antibacterial activity against E. coli, S. aureus and anti-fungal activity against C. albicans. All the synthesized compounds show moderate to good antimicrobial activity.
    Keywords: Cellulose sulphonic acid(CSA), 3, acetyl coumarinn, chalcones, indole, 1, 4, Michael addition, antibacterial activity
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