• Proceedings of the Korea Information Processing Society Conference
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• 2021.05a
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• pp.343-346
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• 2021

약물 디자인이란 단백질과 같은 생물학적 표적에 작용할 수 있는 새로운 약물을 개발하는 과정이다. 전통적인 방법은 탐색과 개발 단계로 구성되어 있으나, 하나의 신약 개발을 위해서는 10 년 이상의 장시간이 요구되기 때문에, 이러한 기간을 단축하기 위한 인공지능 기반의 약물 디자인 방법들이 개발되고 있다. 하지만 많은 심층학습 기반의 약물 디자인 모델들은 RNN 기법을 활용하고 있고, RNN 은 훈련속도가 느리다는 단점이 있기 때문에 개선의 여지가 남아있다. 이런 단점을 극복하기 위해 본 연구는 self-attention 과 variational autoencoder 를 활용한 SMILES 생성 모델을 제안한다. 제안된 모델은 최신 약물 디자인 모델 대비 훈련 시간을 1/36 단축하고, 뿐만 아니라 유효한 SMILES 를 더 많이 생성하는 것을 확인하였다.

• KIPS Transactions on Software and Data Engineering
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• v.11 no.1
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• pp.11-18
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• 2022

De novo drug design is the process of developing new drugs that can interact with biological targets such as protein receptors. Traditional process of de novo drug design consists of drug candidate discovery and drug development, but it requires a long time of more than 10 years to develop a new drug. Deep learning-based methods are being studied to shorten this period and efficiently find chemical compounds for new drug candidates. Many existing deep learning-based drug design models utilize recurrent neural networks to generate a chemical entity represented by SMILES strings, but due to the disadvantages of the recurrent networks, such as slow training speed and poor understanding of complex molecular formula rules, there is room for improvement. To overcome these shortcomings, we propose a deep learning model for SMILES string generation using variational autoencoders with self-attention mechanism. Our proposed model decreased the training time by 1/26 compared to the latest drug design model, as well as generated valid SMILES more effectively.

• Bulletin of the Korean Chemical Society
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• v.33 no.1
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• pp.39-42
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• 2012

The use of Smiles rearrangement in Ugi-type couplings with tropolone allows very straightforward multicomponent formation of 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives. The Ugi four-component reaction of isocyanides with tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one), primary amines and aldehydes proceeds smoothly and cleanly under mild conditions to afford 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives in fairly good yields.

• Bulletin of the Korean Chemical Society
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• v.34 no.2
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• pp.585-589
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• 2013

Optically active N-benzyl-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-ones and N-benzyl-2-methyl-2H-benzo[b][1,4]thiazin-3(4H)-ones with potential synthetic and pharmacological interest were prepared via Smiles rearrangement in conventional as well as microwave irradiation conditions in one-pot from inexpensive (S)-2-chloropropionic acid. Most of the compounds displayed good inhibition against Gram positive bacteria and fungi in the antibiotic test.

• Bulletin of the Korean Chemical Society
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• v.34 no.2
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• pp.394-398
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• 2013

An efficient process for the synthesis of N-azaaryl anilines via Smiles rearrangement as a tool. A variety of N-azaaryl anilines were generated by the reaction of substituted phenols, substituted anilines, aminopyridines and chloroacetyl chloride or pyridols, under base condition in good to excellent yields.

• Bulletin of the Korean Chemical Society
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• v.34 no.12
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• pp.3881-3884
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• 2013

• Journal of the Korea Fashion and Costume Design Association
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• v.14 no.4
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• pp.29-42
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• 2012

Historically, the pattern and technology of Copts' textiles, who were a minority in Egypt, have been studied a lot in the textile sector due to its unique characteristics. Unlike ones in other regions that appeared around the same time, the overall configuration ratio of the patterns looks exaggerated or distorted because they expressed it plainly by interpreting the world with ordinary people's eyes. Also, because it had used mixed linen and woolen yarns, harsh expression way and the use of various colors have been one of the features in Coptic textiles. Coptic textiles, which have been developed along with the historical development of continued domination from neighboring countries, have expressed the effects of the Roman Empire, Christ, Christianity, and Islam on the pattern of its fabric. This study analyzed its characteristics which make people smile by the way of expressing a simple and humorous representation of the textiles and categorized them as Humoristic Beauty - the aesthetic category of humorous feature. In this study, the Humoristic Beauty in Coptic textiles has been analyzed in terms of the following three smiles; the smiles coincidental with the flow of time, the smiles made by the shaping of distorted proportions and appearance, and the smiles like folk-paintings made by a rustic expression way. This study shows the possibility of the further studies on the textile patterns history from a different angle. I look forward to more detailed analysis in the follow-up studies in the future.

• Journal of the Korean Chemical Society
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• v.56 no.4
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• pp.468-472
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• 2012

Efficient one-pot microwave-assisted synthesis of various benzo-[1,4]-oxazinones via Smiles rearrangement is described. Treatment of 2-chloroacetamide, substituted 2-chlorophenols and cesium carbonate in MeO-PEG-OMe (2,000) as solvent afforded the corresponding benzo-[1,4]-oxazinones and 1H-pyrido[2,3-b][1,4]-oxazin-2-(3H)-one as moderate yield.

• Bulletin of the Korean Chemical Society
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• v.29 no.7
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• pp.1379-1385
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• 2008

Highly efficient synthesis of substituted benzo[1,4]oxazin-3-ones and pyrido[1,4]oxazin-2-ones under microwave irradiation via Smiles rearrangement is reported. Substituted benzo[1,4]oxazin-3-ones and pyrido[1,4]oxazin-2-ones were obtained by treatment of substituted 2-chlorophenols or 2-chloropyridols with N-substituted 2-chloroacetamide in the presence of potassium carbonate in MeCN and subsequent exposure to cesium carbonate in DMF. All the reactions which take 2-10 hours under conventional condition were completed successfully within a few minutes under microwave irradiation giving moderate to excellent yields.

• Bulletin of the Korean Chemical Society
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• v.30 no.6
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• pp.1325-1330
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• 2009

A general method has been developed for the solid phase synthesis of drug-like 7-aryl-benzo[b][1,4]oxazin-3(4H)- one derivatives 6. The method relies on a novel, microwave irradiation promoted cyclization reaction of the BOMBA resin bound, N-substituted-$\alpha$-(2-chloro-4-bromophenoxy)acetamide 3 that takes place via a Smiles rearrangement. The 7-bromobenzo[1,4]oxazine 4, produced in this process is converted to 7-aryloxazin analogs 5 by utilizing Suzuki coupling with various substituted arylboronic acids. Finally, the target 7-aryl-benzo[b][1,4]oxazin-3(4H)-ones 6 are liberated from the resin by treatment with 5% TFA. The progress of the reactions involved in this preparative route can be monitored by using ATR-FTIR spectroscopy on a single bead. The target compounds, obtained by using this five-step sequence, are produced in high yields and purities.