A practical synthesis of an anthracyclinone synthon

1983 ◽  
Vol 61 (3) ◽  
pp. 562-564 ◽  
Author(s):  
Chiu-Ming Wong ◽  
Hing-Yat Lam ◽  
Wasimul Haque ◽  
Ai-Qiao Mi ◽  
Gui-Shu Yang
Keyword(s):  
Large Scale ◽  
Allyl Bromide ◽  
High Yield ◽  
Antitumor Drugs ◽  
One Pot ◽  
Claisen Condensation ◽  
Trifluoracetic Acid ◽  
Important Intermediate ◽  
Practical Synthesis

The important intermediate 2-acetyl-5,8-dimethoxytetralin (8) in the syntheses of anthracycline antitumor drugs is easily prepared in high yield on a large scale. Conversion of 2,4-pentanedione to 3-(2,5-dimethoxybenzyl)-hex-5-en-2-one (9) was carried out in a three-step, one-pot process by C-alkylating it with 2,5-dimethoxybenzyl bromide, then allyl bromide followed by a retro-Claisen condensation. Conversion of 9 to the tetralin (8) was done first by ozonolysis to the aldehyde (10) followed by cyclization and reduction of the latter by trimethylsilane in trifluoracetic acid – acetone.

Practical Synthesis of 2'-5'-Linked Oligoadenylates (2-5A Oligomers)

1992 ◽  
Vol 45 (1) ◽  
pp. 205 ◽  
Author(s):  
R Noyori ◽  
M Uchiyama ◽  
T Nobori ◽  
M Hirose ◽  
Y Hayakawa
Keyword(s):  
Ethyl Acetate ◽  
Second Order ◽  
High Yield ◽  
Similar Reaction ◽  
Reaction Sequence ◽  
Facile Synthesis ◽  
One Pot ◽  
Subsequent Oxidation ◽  
Practical Synthesis ◽  
Related Compounds

A general, facile synthesis of 2'-5'-linked oligonucleotides (2-5A oligomers ) has been achieved based on the second-order regioselective protection of adenosine, one-pot formation of the 2'5' internucleotide linkage, and O-selective phosphorylation of N-unblocked nucleosides. Standard t- butyldimethylsilylation of 5'-O-p-methoxytrityladenosine followed by careful recrystallization from a mixture of triethylamine , methanol, ethyl acetate and ether (4 : 4 : 5 : 100 v/v) gives the 3',5'-di-O-protected adenosine in high yield. Magnesium alkoxide -mediated condensation of the 2'-O-free adenosine with o-chlorophenyl p-nitrophenyl phosphorochloridate followed by 2',3'-di-O-t-butyldimethylsilyladenosine produces the N-free and fully O-protected adenylyl (2'-5')adenosine. The resulting adenylyl dimer, after removal of the 5'-O-trityl protector, is elongated to the protected trimeric compound through a similar reaction sequence. Deprotection of the product furnishes the 2-5A core. Condensation of the 5?-0-detritylated core and bis (2,2,2-trichloroethyl) phosphorochloridite assisted by 2,6-lutidine and subsequent oxidation with aqueous iodine produces, after deblocking, 2-5A 5'-monophosphate (p5'A2'p5'pA2'p5'A). The 2-5A 5'-monophosphate is converted into 2-5A 5'-triphosphate (ppp5'A2'p5'A2'p5'A) by reaction with N,N'-carbonyldiimidazole in the presence of triethylamine followed by tributylammonium diphosphate. This procedure allows ready synthesis of 2-5A oligomers and related compounds on a multigram scale.

scholarly journals A two-phase bromination process using tetraalkylammonium hydroxide for the practical synthesis of α-bromolactones from lactones

2021 ◽  
Vol 17 ◽  
pp. 2906-2914
Author(s):  
Yuki Yamamoto ◽  
Akihiro Tabuchi ◽  
Kazumi Hosono ◽  
Takanori Ochi ◽  
Kento Yamazaki ◽  
...  
Keyword(s):  
Large Scale ◽  
Phase System ◽  
Methyl Ethyl ◽  
Two Phase ◽  
One Pot ◽  
Mild Conditions ◽  
Substoichiometric Amount ◽  
Practical Synthesis ◽  
Industrial Use

A simple and efficient method for α-brominating lactones that affords α-bromolactones under mild conditions using tetraalkylammonium hydroxide (R4N+OH−) as a base was developed. Lactones are ring-opened with Br2 and a substoichiometric amount of PBr3, leading to good yields of the corresponding α-bromocarboxylic acids. Subsequent intramolecular cyclization over 1 h using a two-phase system (H2O/CHCl3) containing R4N+OH− afforded α-bromo lactones in good yields. This method can be applied at the 10 mmol scale using simple operations. α-Bromo-δ-valerolactone, which is extremely reactive and difficult to isolate, could be isolated and stored in a freezer for about one week using the developed method. Optimizing the solvent for environmentally friendly large-scale syntheses revealed that methyl ethyl ketone (MEK) was as effective. In addition, in situ-generated α-bromo-δ-valerolactone was directly converted into a sulfur-substituted functional lactone without difficulty by reacting it with a sulfur nucleophile in one pot without isolation. This new bromination system is expected to facilitate the industrial use of α-bromolactones as important intermediates.

scholarly journals Simple one-pot green method for large-scale production of mesalamine, an anti-inflammatory agent

2019 ◽  
Vol 8 (1) ◽  
pp. 320-323
Author(s):  
C. Vijaya Lakshmi ◽  
Naresh Kumar Katari ◽  
Sreekantha B. Jonnalagadda
Keyword(s):  
Large Scale ◽  
Hydroxyl Group ◽  
High Yield ◽  
Scale Production ◽  
One Pot ◽  
Nitrobenzoic Acid ◽  
Green Approach ◽  
Large Scale Production ◽  
Synthesis Protocol ◽  
C Nmr

Abstract We report a rapid and efficient synthesis protocol for mesalamine via a green approach with 2-chloro-5-nitrobenzoic acid as the starting material, for its large-scale production. This one-pot method involves the conversion of a chloro group into a hydroxyl group using aqueous KOH solution, followed by the reduction of a nitro group to amine using Pd/C. The product was characterised and confirmed by 1H-nuclear magnetic resonance (NMR), 13C NMR, IR and mass spectrometry techniques. The salient features of the method include excellent conversion (99.3%), high yield (93%), cost effectiveness and validated results for benign, large-scale production.

The Efficient Synthesis of 1,3-Diallyloxy-2-Propanol without Solvent

2011 ◽  
Vol 311-313 ◽  
pp. 2106-2109
Author(s):  
Xi Mei Liu ◽  
Yu Hu ◽  
Li Hua Feng
Keyword(s):  
Allyl Alcohol ◽  
Large Scale ◽  
Room Temperature ◽  
Low Cost ◽  
High Yield ◽  
Scale Production ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Large Scale Production

An efficient and practical protocol for the preparation of 1,3-diallyloxy-2-propanol has been developed by one-pot reaction between epichlorohydrin and allyl alcohol in the presence of KOH without solvent at room temperature. This preliminary approach provides an environmentally-friendly synthetic route to 1,3-diallyloxy-2-propanol with many advantages, i. e., low cost, high yield, easy purification, mild reaction conditions, and large scale production.

scholarly journals Single-Step Organization of Plasmonic Gold Metamaterials with Self-Assembled DNA Nanostructures

Research ◽  
2019 ◽  
Vol 2019 ◽  
pp. 1-10 ◽  
Author(s):  
Shaokang Ren ◽  
Jun Wang ◽  
Chunyuan Song ◽  
Qian Li ◽  
Yanjun Yang ◽  
...  
Keyword(s):  
Large Scale ◽  
Single Step ◽  
High Yield ◽  
Great Promise ◽  
Dna Nanostructures ◽  
One Pot ◽  
Dna Tiles ◽  
Surface Enhanced Raman ◽  
Self Assembled ◽  
The One

Self-assembled DNA nanostructures hold great promise as nanoscale templates for organizing nanoparticles (NPs) with near-atomistic resolution. However, large-scale organization of NPs with high yield is highly desirable for nanoelectronics and nanophotonic applications. Here, we design five-strand DNA tiles that can readily self-assemble into well-organized micrometer-scale DNA nanostructures. By organizing gold nanoparticles (AuNPs) on these self-assembled DNA nanostructures, we realize the fabrication of one- and two-dimensional Au nanostructures in single steps. We further demonstrate the one-pot synthesis of Au metamaterials for highly amplified surface-enhanced Raman Scattering (SERS). This single-step and high-yield strategy thus holds great potential for fabricating plasmonic metamaterials.

Synthesis of Highly Functionalized Quinazoline-2,4(1H,3H)-diones from Isocyanides, Aniline and Isocyanate via Cu-Catalyzed Intermolecular C-H Activation Reactions

2020 ◽  
Vol 17 (11) ◽  
pp. 832-836
Author(s):  
Manijeh Nematpour ◽  
Hossein Fasihi Dastjerdi ◽  
Mehdi Jahani ◽  
Sayyed Abbas Tabatabai
Keyword(s):  
13C Nmr ◽  
Reaction Times ◽  
High Yield ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Activation Reaction ◽  
Elemental Analyses

A simple and appropriate procedure for the synthesis of quinazoline-2,4(1H,3H)-dione derivatives from isocyanides, aniline and isocyanate via the Cu-catalyzed intramolecular C-H activation reaction is reported. The advantages of this method are one-pot conditions, accessible starting materials- catalyst, high yield of products, and short reaction times. The structures are confirmed spectroscopically (1H- and 13C-NMR, IR and EI-MS) and by elemental analyses.

A Simple Synthesis of the Anticancer Drug Altretamine

2020 ◽  
Vol 17 (8) ◽  
pp. 628-630
Author(s):  
Vu Binh Duong ◽  
Pham Van Hien ◽  
Tran Thai Ngoc ◽  
Phan Dinh Chau ◽  
Tran Khac Vu
Keyword(s):  
Aqueous Solution ◽  
Anticancer Drug ◽  
Potassium Hydroxide ◽  
Large Scale ◽  
Synthesis Method ◽  
Practical Method ◽  
Cyanuric Chloride ◽  
Simple Synthesis ◽  
High Yield ◽  
One Step

A simple and practical method for the synthesis on a large scale of altretamine (1), a wellknown antitumor drug, has been successfully developed. The synthesis method involves the conversion of cyanuric chloride (2) into altretamine (1) by dimethylamination of 2 with an aqueous solution of 40% dimethylamine and potassium hydroxide in 1, -dioxan 4in one step to give altretamine (1) in high yield.

An Efficient and Improved Process for the Synthesis of Itopride Hydrochloride and Trimethobenzamide Hydrochloride

2018 ◽  
Vol 15 (4) ◽  
pp. 572-575 ◽  
Author(s):  
Ponnusamy Kannan ◽  
Samuel I.D. Presley ◽  
Pallikondaperumal Shanmugasundaram ◽  
Nagapillai Prakash ◽  
Deivanayagam Easwaramoorthy
Keyword(s):  
Large Scale ◽  
Hydroxylamine Hydrochloride ◽  
Scale Production ◽  
One Pot ◽  
Hydrochloride Salt ◽  
Environmental Friendly ◽  
Large Scale Production ◽  
Non Ulcer Dyspepsia ◽  
Itopride Hydrochloride ◽  
Yield And Purity

Aim and Objective: Itopride is a prokinetic agent used for treating conditions like non-ulcer dyspepsia. Itopride is administered as its hydrochloride salt. Trimethobenzamide is used for treating nausea and vomiting and administered as its hydrochloride salt. The aim is to develop a novel and environmental friendly method for large-scale production of itopride and trimethobenzamide. Materials and Methods: Itopride and trimethobenzamide can be prepared from a common intermediate 4- (dimethylaminoethoxy) benzyl amine. The intermediate is prepared from one pot synthesis using Phyrdroxybenzaldehye and zinc dust and further reaction of the intermediate with substituted methoxy benzoic acid along with boric acid and PEG gives itopride and trimethobenzamide. Results: The intermediate 4-(dimethylaminoethoxy) benzylamine is prepared by treating p-hydroxybenzaldehyde and 2-dimethylaminoethyl chloride. The aldehyde formed is treated with hydroxylamine hydrochloride. The intermediate is confirmed by NMR and the purity is analysed by HPLC. Conclusion: Both itopride and trimethobenzamide were successfully synthesized by this method. The developed method is environmental friendly, economical for large-scale production with good yield and purity.

Design, Synthesis, In vitro Cytotoxic Activity Evaluation, and Study of Apoptosis Inducing Effect of New Styrylimidazo[1,2-a]Pyridines as Potent Anti-Breast Cancer Agents

2019 ◽  
Vol 19 (2) ◽  
pp. 265-275 ◽  
Author(s):  
Faeze Khalili ◽  
Sara Akrami ◽  
Malihe Safavi ◽  
Maryam Mohammadi-Khanaposhtani ◽  
Mina Saeedi ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Cytotoxic Activity ◽  
High Yield ◽  
Breast Cancer Cell Lines ◽  
Pyridine Derivatives ◽  
One Pot ◽  
Standard Drug ◽  
Three Component Reaction ◽  
Anti Cancer

Background: This paper reports synthesis, cytotoxic activity, and apoptosis inducing effect of a novel series of styrylimidazo[1,2-a]pyridine derivatives. Objective: In this study, anti-cancer activity of novel styrylimidazo[1,2-a]pyridines was evaluated. Methods: Styrylimidazo[1,2-a]pyridine derivatives 4a-o were synthesized through a one-pot three-component reaction of 2-aminopyridines, cinnamaldehydes, and isocyanides in high yield. All synthesized compounds 4a-o were evaluated against breast cancer cell lines including MDA-MB-231, MCF-7, and T-47D using MTT assay. Apoptosis was evaluated by acridine orange/ethidium bromide staining, cell cycle analysis, and TUNEL assay as the mechanism of cell death. Results: Most of the synthesized compounds exhibited more potent cytotoxicity than standard drug, etoposide. Induction of apoptosis by the most cytotoxic compounds 4f, 4g, 4j, 4n, and 4m was confirmed through mentioned methods. Conclusion: In conclusion, these results confirmed the potency of styrylimidazo[1,2-a]pyridines for further drug discovery developments in the field of anti-cancer agents.

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