- HETEROARYL COMPOUNDS FOR TREATMENT OF COMPLEMENT FACTOR D MEDIATED DISORDERS
-
Compounds, methods of use, and processes for making inhibitors of complement factor D or a pharmaceutically acceptable salt or composition thereof are provided. The inhibitors described herein target factor D and inhibit or regulate the complement cascade. The inhibitors of factor D described herein reduce the excessive activation of complement.
- -
-
Paragraph 112; 146-147
(2021/08/27)
-
- A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study
-
Novel and efficient Mn(OAc)3?2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.
- Xu, Meng-Meng,Kou, Lu-Yao,Bao, Xiao-Guang,Xu, Xiao-Ping,Ji, Shun-Jun
-
supporting information
p. 1915 - 1919
(2021/03/09)
-
- Rh(III)-Catalyzed [5 + 1] Annulation of Indole-enaminones with Diazo Compounds to Form Highly Functionalized Carbazoles
-
A novel Rh(III)-catalyzed C-H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic is that this transformation could smoothly furnish a novel [5 + 1] cyclization product with good to excellent yields (up to 95%), accompanied by the thorough removal of acetyl and N,N-dimethyl groups of two substrates from the target products, rather than the normally expected [4 + 2] cyclization products.
- Jiang, Zhidong,Liu, Hong,Zhou, Jianhui,Zhou, Yu,Zhu, Haoran
-
supporting information
p. 4406 - 4410
(2021/06/28)
-
- Cascade Reaction to Selectively Synthesize Multifunctional Indole Derivatives by IrIII-Catalyzed C?H Activation
-
An effective and condition-controlled way to synthesize with high selectivity a variety of functionalized indoles with potent biological properties has been developed. Notably, 2,4-dialkynyl indole products were obtained by direct double C?H bond alkynylation, whereas alkynyl at the C4 position could convert to carbonyl to generate 2-alkynyl-3,4-diacetyl indoles fast and effectively. Additionally, a one-pot relay catalytic reaction led to 2,5-di-alkynyl-3,4-diacetyl indoles when using a carbonyl group as the directing group and by controlling the type and quantity of additives. A possible mechanism was proposed based on many studies including deuterium-exchange experiments, the necessary conditions of product conversion, and the effect of water on the reaction.
- Chai, Xin-Yue,Xu, Hui-Bei,Dong, Lin
-
supporting information
p. 13123 - 13127
(2021/08/13)
-
- Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains
-
Infections caused due to multidrug resistant organisms have emerged as a constant menace to human health. Even though numerous antibiotics are currently available for treating infectious diseases, a great number of bacterial strains have acquired resistance to many of them. Among these, infections caused due to Staphylococcus aureus are predominant in adult and paediatric population. Indole is a prominent chemical scaffold found in many pharmacologically active natural products and synthetic drugs. A number of oxime ether containing compounds have attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among all, compound 5h was found to possess potent activity against susceptible as well as MRSA and VRSA strains of S. aureus with MIC of 1 μg/mL and 2–4 μg/mL respectively. In addition, compound 5h was found to be non-toxic to Vero cells and exhibited good selectivity index of >40. Further, 5h, E-9a and E-9b possessed good biofilm inhibition against S. aureus. With these assuring biological properties, synthesized compounds could be potential prospective antimicrobial agents.
- Akunuri, Ravikumar,Veerareddy, Vaishnavi,Kaul, Grace,Akhir, Abdul,Unnissa, Tanveer,Parupalli, Ramulu,Madhavi,Chopra, Sidharth,Nanduri, Srinivas
-
-
- Natural product Pimprinine derivative as well as preparation method and application thereof
-
The invention discloses a Pimprinine derivative as shown in a formula III in the description. The invention also discloses a preparation method of the Pimprinine derivative, and a series of Pimprinine derivatives are synthesized by taking Pimprinine as a lead, combining the structural characteristics of Pimprinine, taking cheap and easily available indole as a raw material, modifying and transforming different sites of a framework structure of the indole and introducing different substituent groups. The Pimprinine derivative disclosed by the invention has good bactericidal activity, shows efficient and/or broad-spectrum bactericidal activity, and can be applied to crop diseases caused by fungi, bacteria and viruses.
- -
-
Paragraph 0079-0082; 0085
(2021/07/31)
-
- NbCl5 and AgClO4 promoted regio-selective acylation of indoles
-
In present study, an efficient and simple strategy towards chemo-selective and regio-selective acylation of indole using NbCl5 and AgClO4 catalyst are reported. This method utilizes the catalytic potentiality of NbCl5 and AgClO4 towards acylation of unprotected indoles in a synergistic manner. The combination of these catalytic system results into numerous advantages such as excellent yields of product, short reaction times and easier isolation of products.
- Kamble, Narendra R.,Pawar, Hari R.,Kamble, Vinod T.
-
p. 317 - 321
(2020/01/08)
-
- Weak Coordination Enabled Switchable C4-Alkenylation and Alkylation of Indoles with Allyl Alcohols
-
A weak carbonyl coordination facilitated tunable reactivity between alkenylation and alkylation of indoles at the C4 C-H site is presented using readily accessible allylic alcohols in the presence of Rh catalysis by switching the additives or directing group. Exclusive site selectivity, functional group tolerance, and late-stage modifications are the important practical features.
- Banerjee, Sonbidya,De, Pinaki Bhusan,Mishra, Manmath,Pradhan, Sourav,Punniyamurthy, Tharmalingam
-
supporting information
(2020/03/11)
-
- Second-Generation Meridianin Analogues Inhibit the Formation of Mycobacterium smegmatis Biofilms and Sensitize Polymyxin-Resistant Gram-Negative Bacteria to Colistin
-
Drug-resistant bacteria are rapidly becoming a significant problem across the globe. One element that factors into this crisis is the role played by bacterial biofilms in the recalcitrance of some infections to the effects of conventional antibiotics. Bacteria within a biofilm are highly tolerant of both antibiotic treatment and host immune responses. Biofilms are implicated in many chronic infections, including tuberculosis, in which they can act as bacterial reservoirs, requiring an arduous antibiotic regimen to eradicate the infection. A separate, compounding problem is that antibiotics once seen as last-resort drugs, such as the polymyxin colistin, are now seeing more frequent usage as resistance to front-line drugs in Gram-negative bacteria becomes more prevalent. The increased use of such antibiotics inevitably leads to an increased frequency of resistance. Drugs that inhibit biofilms and/or act as adjuvants to overcome resistance to existing antibiotics will potentially be an important component of future approaches to antibacterial treatment. We have previously demonstrated that analogues of the meridianin natural product family possess adjuvant and antibiofilm activities. In this study, we explore structural variation of the lead molecule from previous studies, and identify compounds showing both improved biofilm inhibition potency and synergy with colistin.
- Melander, Christian,Melander, Roberta J.,Zeiler, Michael J.
-
supporting information
p. 1672 - 1679
(2020/08/05)
-
- Ketone-Directed Cobalt(III)-Catalyzed Regioselective C2 Amidation of Indoles
-
An efficient cobalt(III)-catalyzed method for the direct C-H amidation of unprotected indoles for 2-amino indole scaffold construction has been developed. With dioxazolone as the amidating reagent, a variety of 2-amino indole derivatives were achieved in moderate to excellent yields using an organic acid as the additive and a ketone as the directing group.
- Shi, Xinxia,Xu, Weiyan,Wang, Rongchao,Zeng, Xiaofei,Qiu, Huayu,Wang, Min
-
p. 3911 - 3920
(2020/03/23)
-
- AMIDE SUBSTITUTED INDOLE COMPOUNDS USEFUL AS TLR INHIBITORS
-
N-oxides, or salts thereof, wherein G, L2, R1, R5, R9, R10, and n are defined herein. Also disclosed are methods of using such compounds as inhibitors of signaling through Toll-like receptor 7, or 8,
- -
-
Page/Page column 73
(2019/07/13)
-
- Weak Coordination-Guided Regioselective Direct Redox-Neutral C4 Allylation of Indoles with Morita-Baylis-Hillman Adducts
-
A weak carbonyl coordination-guided regioselective C4 allylation of indoles is demonstrated using the versatile Morita-Baylis-Hillman adduct in the presence of Rh catalysts in a redox-neutral fashion. The substrate scope, functional group diversity, oxidant free character, mechanistic aspects, and synthetic utilities are important practical features.
- Pradhan, Sourav,De, Pinaki Bhusan,Punniyamurthy, Tharmalingam
-
supporting information
p. 9898 - 9903
(2019/12/24)
-
- Feasible selective synthesis of 3-Acetylindoles and 3-Acetoacetylindoles from β-ethylthio-β-indoly α, β-unsaturated ketones
-
An efficient and selective synthesis of 3-acetyl free(N-H)/N-substituded indoles and 3-acetoacetyl free(N-H)/N-substituded indoles has been developed via the hydrolysis reaction of β-ethylthio-β-indoly α, β-unsaturated ketones in the presence of 3 equivalent of NaOH and 5 mol% of H2SO4, respectively. The procedure features easy operation, excellent yields, and high selectivity, compatibility and practicability.
- Wang, Wen-Ju,Yu, Hai-Feng
-
p. 377 - 385
(2019/02/07)
-
- PYRIDYL SUBSTITUTED INDOLE COMPOUNDS
-
Disclosed are compounds of Formula (I) N-oxide, or salt thereof, wherein R1, R2, R3, R4, R5, m, n, and p are defined herein. Also disclosed are methods of using such compounds as inhibitors of signaling through Toll-like receptor 7, or 8, or 9, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating inflammatory and autoimmune diseases.
- -
-
Page/Page column 90
(2018/03/28)
-
- Rhodium(III)-Catalyzed Regioselective Direct C4-Alkylation and C2-Annulation of Indoles: Straightforward Access to Indolopyridone
-
A straightforward RhIII-catalyzed strategy was developed for the site-selective C4-alkylation and C2-annulation of indole by using electronically variable diazo esters. The transformation was accomplished with the assist of an oxime directing group at the C3 position of the indole core with wide scope and functional-group tolerance. The method directly provided an indolopyridone core. The selectivity was triggered by the reactivity of the diazo coupling partner.
- Biswas, Aniruddha,Samanta, Rajarshi
-
p. 1426 - 1436
(2018/04/06)
-
- Meridianin D Analogues Display Antibiofilm Activity against MRSA and Increase Colistin Efficacy in Gram-Negative Bacteria
-
In the last 30 years, development of new classes of antibiotics has slowed, increasing the necessity for new options to treat multidrug resistant bacterial infections. Development of antibiotic adjuvants that increase the effectiveness of currently available antibiotics is a promising alternative approach to classical antibiotic development. Reports of the ability of the natural product meridianin D to modulate bacterial behavior have been rare. Herein, we describe the ability of meridianin D to inhibit biofilm formation of methicillin-resistant Staphylococcus aureus (MRSA) and to increase the potency of colistin against colistin-resistant and sensitive Gram-negative bacteria. Analogues were identified that are capable of inhibiting and dispersing MRSA biofilms and lowering the colistin MIC to below the CLSI breakpoint against Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli.
- Huggins, William M.,Barker, William T.,Baker, James T.,Hahn, Nicholas A.,Melander, Roberta J.,Melander, Christian
-
p. 702 - 707
(2018/06/04)
-
- Oxidative coupling of enolates using memory of chirality: An original enantioselective synthesis of quaternary α-amino acid derivatives
-
We describe here the first enantioselective oxidative heterocoupling of enolates. Our strategy relies on the memory of chirality concept and allows the stereocontrolled formation of quaternary centres on α-amino acid derivatives with an enantiomeric excess of up to 94%.
- Mambrini, Antonin,Gori, Didier,Guillot, Régis,Kouklovsky, Cyrille,Alezra, Valérie
-
supporting information
p. 12742 - 12745
(2018/12/01)
-
- ARYL, HETEROARYL, AND HETEROCYCLIC COMPOUNDS FOR TREATMENT OF IMMUNE AND INFLAMMATORY DISORDERS
-
Compounds, methods of use, and processes for making inhibitors of complement Factor D are provided comprising Formula I, I" and I'" or a pharmaceutically acceptable salt or composition thereof. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade. The inhibitors of Factor D described herein reduces the excessive activation of complement.
- -
-
Paragraph 0923
(2017/03/14)
-
- ALKYNE COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS
-
Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is alkyne substituent (R32) are provided. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade. The inhibitors of Factor D described herein can reduce the excessive activation of complement.
- -
-
Paragraph 0548
(2017/03/14)
-
- AMINO COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS
-
Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is an amino substituent (R32) are provided. The inhibitors of Factor D described herein reduce the excessive activation of complement.
- -
-
Paragraph 0518; 0519
(2017/03/14)
-
- ARYL, HETEROARYL, AND HETEROCYCLIC COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS
-
Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is an aryl, heteroaryl or heterocycle (R32) are provided. The inhibitors of Factor D described herein reduce the excessive activation of complement.
- -
-
Page/Page column 143; 147; 172
(2017/03/14)
-
- Three-Component Coupling-Oxidative Amidation-Heterocycloannulation: Synthesis of the Indole Alkaloids Hamacanthin A and trans -2,5-Bis(3′-Indolyl)piperazine
-
Concise and highly convergent syntheses of antifungal marine bis(indole) alkaloids, hamacanthin A and trans-2,5-bis(3′-indolyl)piperazine is described. The total synthesis of hamacanthin A is accomplished via the oxidative amidation-chemoselective heterocycloannulation of 2,2-dibromo-1-(1H-indol-3-yl)ethanone with 1-(1H-indol-3-yl)ethane-1,2-diamine. The reduction of desbromo hamacanthin with aluminum borohydride afforded the alkaloid trans-2,5-bis(3′-indolyl)piperazine. Two novel and convenient protocols for the synthesis of indolyl-1,2-diaminoethane are also developed in moderate to good yields.
- Srinivasan, A. Kaliyaperumal,Banerjee, Shyamapada,Pachore, Sharad S.,Syam Kumar
-
supporting information
p. 1057 - 1064
(2017/05/19)
-
- Novel iron and gallium salts of Aquivion PFSA: Synthesis, characterization and some catalytic applications
-
The objective of this study was to prepare, characterize and test the catalytic properties of iron and gallium salts of Aquivion PFSA (hereinafter Aquivion-H). The samples were characterized by the determination of metal loading in fresh and used materials, ATR-FTIR, and thermogravimetric analysis (TG-DSC). The salts were screened in Friedel-Crafts acylation of some heterocyclic compounds and compared with some homogeneous and heterogeneous Lewis acids as well as with pure Aquivion-H. These new salts revealed efficient catalytic activity and recyclability.
- Tassini, Riccardo,Rathod, Vikas D.,Paganelli, Stefano,Balliana, Eleonora,Piccolo, Oreste
-
p. 257 - 263
(2015/11/23)
-
- BIS-INDOLE ALKALOIDS FOR USE IN THE TREATMENT OF INFECTIONS
-
The present application describes bisindole alkaloids of formulas I and II and pharmaceutical compositions thereof useful in the treatment of bacterial infection such as Staphylococcus aureus (MRSA) infection: wherein X1 is: wherein X2 is:
- -
-
Page/Page column 33; 34; 36
(2016/02/29)
-
- Synthetic analogues of the marine bisindole deoxytopsentin: Potent selective inhibitors of MRSA pyruvate kinase
-
As part of an ongoing study to elucidate the SAR of bisindole alkaloid inhibitors against the evolutionary conserved MRSA pyruvate kinase (PK), we present here the synthesis and biological activity of six dihalogenated analogues of the naturally occurring sponge metabolite deoxytopsentin, including the naturally occurring dibromodeoxytopsentin. The most active compounds displayed potent low nanomolar inhibitory activity against MRSA PK with concomitant significant selectivity for MRSA PK over human PK orthologues. Computational studies suggest that these potent MRSA PK inhibitors occupy a region of the small interface of the enzyme tetramer where amino acid sequence divergence from common human PK orthologues may contribute to the observed selectivity.
- Veale, Clinton G. L.,Zoraghi, Roya,Young, Ryan M.,Morrison, James P.,Pretheeban, Manoja,Lobb, Kevin A.,Reiner, Neil E.,Andersen, Raymond J.,Davies-Coleman, Michael T.
-
supporting information
p. 355 - 362
(2015/04/14)
-
- Meridianin derivatives as potent Dyrk1A inhibitors and neuroprotective agents
-
Meridianins are a group of marine-derived indole alkaloids which are reported to possess kinase inhibitory activities. In the present Letter, we report synthesis of N1-substituted and C-ring modified meridianin derivatives and their evaluation as Dyrk1A inhibitors and neuroprotective agents. Among the library of 52 compounds screened, morpholinoyl linked derivative 26b and 2-nitro-4-trifluoromethyl phenyl sulfonyl derivative 29v displayed potent inhibition of Dyrk1A with IC50 values of 0.5 and 0.53 μM, respectively. The derivative 26b also inhibited Dyrk2 and Dyrk3 with IC50 values of 1.4 and 2.2 μM, respectively showing 2.2 and 4.4 fold selectivity for Dyrk1A with respect to Dyrk2 and Dyrk3. The compound 26b was not cytotoxic to human neuroblastoma SH-SY5Y cells (IC50 >100 μM) and it displayed significant neuroprotection against glutamate-induced neurotoxicity in these cells at 10 μM. Molecular modelling studies of compound 26b led to identification of key interactions in the binding site of Dyrk1A and the possible reasons for observed Dyrk1A selectivity over Dyrk2.
- Yadav, Rammohan R.,Sharma, Sadhana,Joshi, Prashant,Wani, Abubakar,Vishwakarma, Ram A.,Kumar, Ajay,Bharate, Sandip B.
-
p. 2948 - 2952
(2015/06/22)
-
- A simple, effective, green method for the regioselective 3-acylation of unprotected indoles
-
A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.
- Tran, Phuong Hoang,Tran, Hai Ngoc,Hansen, Poul Erik,Do, Mai Hoang Ngoc,Le, Thach Ngoc
-
p. 19605 - 19619
(2015/11/27)
-
- Acid-catalyzed acylation reaction via C-C bond cleavage: A facile and mechanistically defined approach to synthesize 3-acylindoles
-
A facile acid-catalyzed acylation of indoles with 1,3-dione as an eco-friendly acylating agent was developed. This protocol combines C-C bond cleavage and heterocyclic C-H bond functionalization to form new C-C bonds. Based on the detailed mechanistic studies, a credible mechanistic pathway was proposed. This journal is
- Xing, Qi,Li, Pan,Lv, Hui,Lang, Rui,Xia, Chungu,Li, Fuwei
-
supporting information
p. 12181 - 12184
(2014/12/11)
-
- NOVEL BIS-INDOLIC DERIVATIVES, A PROCESS FOR PREPARING THE SAME AND THEIR USES AS A DRUG
-
The present invention relates to novel bis-indolic derivatives, processes for their preparation, and their potential use as new antibacterial drugs.
- -
-
Paragraph 0307; 0308
(2013/03/26)
-
- Novel bis-indolic derivatives, their uses in particular as antibacterials
-
The present invention relates to novel bis-indolic derivatives, processes for their preparation, and their potential use as new antibacterial drugs.
- -
-
Paragraph 0247-0248
(2013/03/26)
-
- BIS-INDOLIC DERIVATIVES, THEIR USES IN PARTICULAR AS ANTIBACTERIALS
-
The present invention relates to novel bis-indolic derivatives, processes for their preparation, and their potential use as new antibacterial drugs.
- -
-
Page/Page column 45
(2013/03/26)
-
- BIS-INDOLIC DERIVATIVES, A PROCESS FOR PREPARING THE SAME AND THEIR USES AS A DRUG
-
The present invention relates to novel bis-indolic derivatives, processes for their preparation, and their potential use as new antibacterial drugs.
- -
-
Page/Page column 61; 62
(2013/03/26)
-
- Meridianin G and its analogs as antimalarial agents
-
The marine-derived indole alkaloids meridianin C and G and their N1-substituted and C-ring modified analogs were synthesized and screened for antiprotozoal and antimicrobial activities. Meridianin C and G showed antimalarial activity against both chloroquine-resistant (D6) as well as sensitive (W2) clones of Plasmodium falciparum with IC50 values in the range of 4.4 to 14.4 μM. Meridianin G showed better activity against the W2 clone, showing a higher selectivity index >24.1. Among the analogs, N1-morpholinoyl meridianin C analog displayed antimalarial activity against both clones, showing selectivity indices up to 25.1. Meridianin C along with a few other analogs showed weak to moderate antileishmanial activity against Leishmania donovani promastigotes, the best analog being a C-ring modified 5-iodo meridianin showing an IC50 of 9.17 μM. A few compounds also showed mild antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus, and antifungal activity against Cryptococcus neoformans.
- Bharate, Sandip B.,Yadav, Rammohan R.,Khan, Shabana I.,Tekwani, Babu L.,Jacob, Melissa R.,Khan, Ikhlas A.,Vishwakarma, Ram A.
-
supporting information
p. 1042 - 1048
(2013/07/27)
-
- Synthesis, protein kinase inhibitory potencies, and in vitro antiproliferative activities of meridianin derivatives
-
The synthesis of new meridianin derivatives is described. The indolic ring system was substituted at the C-4 to C-7 positions either by a bromine atom or by nitro or amino groups. Additionally, an iodine atom or various aryl groups were introduced at the C-5 position of the 2-aminopyrimidine ring. These compounds as well as some of their synthetic intermediates were tested for their kinase inhibitory potencies and for their in vitro antiproliferative activities. We found that this series of compounds is particularly interesting in the development of new inhibitors of DYRK1A and CLK1 kinases. The most effective compounds toward these two kinase families are the 6- and 7-bromo derivatives 30, 33, and 34 that showed more than 45-fold selectivity toward DYRK1A/CLK1 kinases over the other kinases tested. Meridianin derivatives could thus be developed toward potent and selective inhibitors of key RNA splicing regulators and potential therapeutic agents.
- Giraud, Francis,Alves, Georges,Debiton, Eric,Nauton, Lionel,Théry, Vincent,Durieu, Emilie,Ferandin, Yoan,Lozach, Olivier,Meijer, Laurent,Anizon, Fabrice,Pereira, Elisabeth,Moreau, Pascale
-
scheme or table
p. 4474 - 4489
(2011/09/14)
-
- Novel and simple methodology for the synthesis of 3-acetylindoles and their N-alkyl derivatives using TBAB as phase transfer catalyst
-
Using 5% aq. NaOH, a simple method for the transformation of 3-cyanoacetylindoles 2(a-e) into 3-acetylindoles 3 (a-e), in good yields, is reported. Tetrabutylammoniumbromide (TBAB) is found to be an efficient phase transfer catalyst for the synthesis of N-alkyl derivatives 5(a-t) of 3-acetylindoles 3(a-e) giving products in excellent yields. 2 (a-e) were themselves obtained from simple indoles 1 (a-e) by reaction with cyano acetic acid in the presence of propionic anhydride at 100 °C for 5-10 min. Partial hydrolysis of 2 (a-e) under hot acidic conditions yielded the corresponding carboxamides α-(3-indolecarboxoyl)acetamides 4(a-e). Which could be readily transformed into the respective 3(a-e) by refluxing with 5% aq. NaOH for 2-2.5 h.
- Venkatanarayana,Dubey, Pramod K.
-
experimental part
p. 656 - 662
(2012/06/01)
-
- Formyl-and acetylindols: Vibrational spectroscopy of an expectably pharmacologically active compound family
-
In the peresent paper, indole and its seven derivatives were compared, namely 3-formylindole, 1-methyl-3-formylindole, 1-ethyl-3-formylindole, 3-acetylindole, 1-methyl-3-acetylindole, 1-ethyl-3-acetylindole and 1,3-diacetylindole. The substitution of indole in position 3 with aldehydes and with alkyl groups cause only minor changes in the molecular geometry, however, substantially larger alterations are found in the charge distribution and in the vibrational force constants. The appearance of the aldhyde groups increased the degree of association as it was observable on the shape of infrared NH stretching band and its shifts. The alkyl substitution shifts the aldehyde carbonyl stretch band frequencies to somewhat higher values. The effect of the second acetyl group in position 1 is not comparable with those of the 1-alkyl groups. The latter effect is observable in the molecular geometry, however, it is more pronounced in the changes of the net charge distribution, the vibrational force constants and the infrared spectra.
- Billes, Ferenc,Podea, Paula Veronica,Mohammed-Ziegler, Ildikó,To?a, Monica,Mikosch, Hans,Irimie, Dan-Florin
-
experimental part
p. 1031 - 1045
(2012/06/30)
-
- Towards the syntheses of N-H and N-alkylated derivatives of meridianins
-
(Chemical Equation Presented) Novel N-H and N-alkylated derivatives of meridianins have been synthesized as potential antitumor agents by a two-step conversion of N-tosyl-3-acetylindoles or N-alkyl-3-acetylindoles to the corresponding enaminones using DMF-DMA, with or without added pyrrolidine. Further cyclization with guanidine gave the corresponding 2-aminopyrimidines. The structures of the compounds, thus obtained, were proved by 1H and 13C NMR spectroscopy, NOE experiments and X-ray analysis.
- Simon, Ga?lle,Couthon-Gourves, Hélène,Haelters, Jean-Pierre,Corbel, Bernard,Kervarec, Nelly,Michaud, Fran?ois,Meijer, Laurent
-
p. 793 - 801
(2008/03/29)
-
- Synthesis of the indole alkaloids meridianins from the tunicate Aplidium meridianum
-
The marine natural products meridianins A and C-E have been synthesized for the first time starting from the appropriate N-tosyl-3-acetylindole. A facile two-step conversion of N-tosyl-3-acetylindoles to the corresponding meridianins by treatment with dimethylformamide dimethylacetal and further cyclization of the resulting enaminone with aminoguanidine is described. This method has also been applied for the preparation of the 3-[(2-amino)pyrimidin-4-yl]-7-azaindole.
- Fresneda, Pilar M,Molina, Pedro,Bleda, Juan A
-
p. 2355 - 2363
(2007/10/03)
-