Anticancer agent synthesis designed by artificial intelligence: Pd(OAc)2-catalyzed one-pot preparation of biphenyls and its application to a concise synthesis of various diazofluorenes

2020 ◽  
Vol 61 (38) ◽  
pp. 152267
Author(s):  
Tetsuhiko Takabatake ◽  
Hiroki Tomita ◽  
Syo Okada ◽  
Natsumi Hayashi ◽  
Takashi Masuko ◽  
...  
Keyword(s):  
Artificial Intelligence ◽  
Anticancer Agent ◽  
One Pot

One-Pot Solvothermal Synthesis and X-Ray Structure of a Methylated Terpyridine Derivative as DNA Binder and Anticancer Agent

Heterocycles ◽  
2019 ◽  
Vol 98 (3) ◽  
pp. 387 ◽  
Author(s):  
Jintao Wang ◽  
Yihui Jiang ◽  
Keke Chai ◽  
Yi Sun ◽  
Qiwen Pang ◽  
...  
Keyword(s):  
Solvothermal Synthesis ◽  
Anticancer Agent ◽  
One Pot ◽  
X Ray

A Review on Synthetic Approaches of Phenanthridine

2021 ◽  
Vol 18 ◽  
Author(s):  
Nilesh Kshirsagar ◽  
Ratnamala Sonawane ◽  
Sultan Pathan ◽  
Ganesh Kamble ◽  
Girdhar Pal Singh
Keyword(s):  
Biological Activity ◽  
Transition Metal ◽  
Material Science ◽  
Anticancer Agent ◽  
Hypervalent Iodine ◽  
One Pot ◽  
Bond Forming ◽  
Microwave Assisted ◽  
Metal Catalyzed ◽  
Synthetic Approaches

Abstract: The phenanthridine family is widely found in medicinal chemistry and material science because of the biological activity and the presence in a variety of significant natural products and synthetic dye-stuffs. The phenanthridine has many clinical application like anticancer agent, antibacterial, antiprotozoal, pharmaceutically, and optoelectronic properties. Many methods have been reported for the synthesis of phenanthridine and phenanthridine alkaloids such as Pd catalyzed C-C bond forming. Reaction involving C-H activation , Radical, Microwave-assisted , transition metal catalyzed, one- pot cascade, benzyne mediated, photochemical, hypervalent iodine promoted ,etc. Here we summarized the literature data from 2014 to present concerning a novel or improved synthetic approaches.

Discovery of orthogonal synthesis using artificial intelligence: Pd(OAc)2-catalyzed one-pot synthesis of benzofuran and bicyclo[3.3.1]nonane scaffolds

2020 ◽  
Vol 61 (36) ◽  
pp. 152275
Author(s):  
Tetsuhiko Takabatake ◽  
Keisuke Fujiwara ◽  
Sho Okamoto ◽  
Ryo Kishimoto ◽  
Natsuko Kagawa ◽  
...  
Keyword(s):  
Artificial Intelligence ◽  
One Pot ◽  
One Pot Synthesis

scholarly journals An Artificial Intelligence that Discovers Unpredictable Chemical Reactions

2020 ◽  
Author(s):  
Dario Caramelli ◽  
Jaroslaw Granda ◽  
Dario Cambié ◽  
Hessam Mehr ◽  
Alon Henson ◽  
...  
Keyword(s):  
Neural Network ◽  
Artificial Intelligence ◽  
Deep Learning ◽  
Convolutional Neural Network ◽  
Chemical Reactions ◽  
Multicomponent Reaction ◽  
Cascade Reaction ◽  
One Pot ◽  
Single Substrate ◽  
Set Up

<p><b>We present an artificial intelligence, built to autonomously explore chemical reactions in the laboratory using deep learning. The reactions are performed automatically, analysed online, and the data is processed using a convolutional neural network (CNN) trained on a small reaction dataset to assess the reactivity of reaction mixtures. The network can be used to predict the reactivity of an unknown dataset, meaning that the system is able to abstract the reactivity assignment regardless the identity of the starting materials. The system was set up with 15 inputs that were combined in 1018 reactions, the analysis of which lead to the discovery of a ‘multi-step, single-substrate’ cascade reaction and a new mode of reactivity for methylene isocyanides. <i>p</i>-Toluenesulfonylmethyl isocyanide (TosMIC) in presence of an activator reacts consuming six equivalents of itself to yield a trimeric product in high (unoptimized) yield (47%) with formation of five new C-C bonds involving <i>sp</i>-<i>sp<sup>2</sup></i> and <i>sp</i>-<i>sp<sup>3</sup></i> carbon centres. A cheminformatics analysis reveals that this transformation is both highly unpredictable and able to generate an increase in complexity like a one-pot multicomponent reaction.</b></p>

Efficient One-Pot Synthesis of 2,4-Disubstituted Thiazoles and Dimeric Thiazoles Directly from Acyl Chlorides and β-Azido Disulfides

Synthesis ◽  
2017 ◽  
Vol 49 (21) ◽  
pp. 4876-4886 ◽  
Author(s):  
Yi Liu ◽  
Yuguo Du ◽  
Zhi Li ◽  
Yichuan Xie ◽  
Peng He ◽  
...  
Keyword(s):  
Wittig Reaction ◽  
Anticancer Agent ◽  
Acid Chlorides ◽  
Thiazole Derivatives ◽  
One Pot ◽  
Acyl Chlorides ◽  
Mild Conditions ◽  
Pharmacological Evaluation ◽  
Disulfide Cleavage ◽  
High Yields

A simple and effective one-pot cascade procedure to provide 2,4-disubstituted thiazoles and symmetrical dimeric thiazoles directly from commercially available acid chlorides and β-azido disulfides in moderate to high yields is described. This cascade transformation consists of disulfide cleavage, thiocarbonylation, phosphine-promoted intramolecular Staudinger/aza-Wittig reaction and dehydrogenation to form the corresponding thiazoles. The application of our methodology is demonstrated by the concise two-step synthesis of anticancer agent SMART and its O-linked dimer in 64% and 46% overall yields, respectively. This directed cascade reaction could be easily handled and scaled up under mild conditions, enabling the construction of focused thiazole derivatives for further pharmacological evaluation.

scholarly journals An Artificial Intelligence that Discovers Unpredictable Chemical Reactions

2020 ◽  
Author(s):  
Dario Caramelli ◽  
Jaroslaw Granda ◽  
Dario Cambié ◽  
Hessam Mehr ◽  
Alon Henson ◽  
...  
Keyword(s):  
Neural Network ◽  
Artificial Intelligence ◽  
Deep Learning ◽  
Convolutional Neural Network ◽  
Chemical Reactions ◽  
Multicomponent Reaction ◽  
Cascade Reaction ◽  
One Pot ◽  
Single Substrate ◽  
Set Up

<p><b>We present an artificial intelligence, built to autonomously explore chemical reactions in the laboratory using deep learning. The reactions are performed automatically, analysed online, and the data is processed using a convolutional neural network (CNN) trained on a small reaction dataset to assess the reactivity of reaction mixtures. The network can be used to predict the reactivity of an unknown dataset, meaning that the system is able to abstract the reactivity assignment regardless the identity of the starting materials. The system was set up with 15 inputs that were combined in 1018 reactions, the analysis of which lead to the discovery of a ‘multi-step, single-substrate’ cascade reaction and a new mode of reactivity for methylene isocyanides. <i>p</i>-Toluenesulfonylmethyl isocyanide (TosMIC) in presence of an activator reacts consuming six equivalents of itself to yield a trimeric product in high (unoptimized) yield (47%) with formation of five new C-C bonds involving <i>sp</i>-<i>sp<sup>2</sup></i> and <i>sp</i>-<i>sp<sup>3</sup></i> carbon centres. A cheminformatics analysis reveals that this transformation is both highly unpredictable and able to generate an increase in complexity like a one-pot multicomponent reaction.</b></p>

scholarly journals Side-chain opening of steroidal sapogenins to form 22-oxocholestanic skeletons. An approach to analogues of the aglycone of the potent anticancer agent OSW-1

2019 ◽  
Vol 53 (3) ◽  
Author(s):  
María A. Fernández-Herrera ◽  
Jesús Sandoval-Ramírez ◽  
Socorro Meza-Reyes ◽  
Sara Montiel-Smith
Keyword(s):  
Anticancer Agent ◽  
2D Nmr ◽  
Starting Material ◽  
Side Chain ◽  
One Pot ◽  
Mild Conditions ◽  
High Yields

The side-chain opening of 25R and 25S steroidal sapogenins to form 22-oxocholestanic skeletons is described. The transformation was produced under mild conditions providing high yields (70-87%), in a one pot procedure (some acetylated starting material is recovered). This methodology yields 17-deoxy-26-oxy analogues of the aglycone of the potent anticancer agent OSW-1. All products were fully characterized by 1D and 2D NMR; the most representative displacements are briefly discussed.    

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