• 대한화학회지
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• 제57권6호
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• pp.731-737
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• 2013

A convenient synthesis of bifunctional sulfonamide-amide derivatives was reported. Amide coupling of 4-methyl benzoic acid 1 followed by reaction with chlorosulfonic acid produce ethyl-4-(3-(chlorosulfonyl)-4-methylbenzoyl)piperazine-1-carboxylate 4. The resulted compound on further treatment with various anilines produces the title sulfonamide-amide derivatives 5a-n. The configurations of these compounds were established by elemental analysis, IR, $^1H$ NMR, mass spectra, and by their preparation from the corresponding 4-methyl benzoic acid 1 and chlorosulfonic acid. All these new compounds demonstrate significant in vitro antibacterial and antifungal activities against all bacterial and fungal strains.

• Bulletin of the Korean Chemical Society
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• 제35권6호
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• pp.1590-1600
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• 2014

Cinchona-based bifunctional catalysts have been extensively employed in the field of organocatalysis due to the incorporation of both hydrogen-bonding acceptors (quinuclidine) and hydrogen-bonding donors (e.g., alcohol, amide, (thio)urea and squaramide) in the molecule, which can simultaneously activate nucleophiles and electrophiles, respectively. Among them, cinchona-derived (thio)urea and squaramide catalysts have shown remarkable application potential by using their bifurcated hydrogen bonding donors in activating electrophilic carbonyls and imines. However, due to their bifunctional nature, they tend to aggregate via inter- and intramolecular acid-base interactions under certain conditions, which can lead to a decrease in the enantioselectivity of the reaction. To overcome this self-aggregation problem of bifunctional organocatalysts, we have successfully developed a series of sulfonamide-based organocatalysts, which do not aggregate under conventional reaction conditions. Herein, we summarize the recent applications of our cinchona-derived sulfonamide organocatalysts in highly enantioselective methanolytic desymmetrization and decarboxylative aldol reactions. Immobilization of sulfonamide-based catalysts onto solid supports allowed for unprecedented practical applications in the synthesis of valuable bioactive synthons with excellent enantioselectivities.

• 자연과학논문집
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• 제7권
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• pp.47-51
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• 1995

입체 이성질체를 합성하는 방법으로 최근에 알려진 입체선택성 촉매를 이용한 유기반응을 연구 하기 위하여 비천연 아미노산인 인돌린-2- 카르본산으로 부터카르본산그룹의 환원,2차아민기의 보호화,메실화,아지도치환,환원에 의한 아민기로의 전환, 술폰화, 보호기제거등의 총 5단계의 합성과정을 거쳐 목적하는 술폰아미드를 합성하였다. 각 생성물은 관 크로마토그래피에 의하여 분리 정제후 핵자기공명스펙트럼($^1H,^13C $ NMR) 적외선 스펙트럼 등에 의하여 구조를 확인 하였다.

• The Korean Journal of Physiology and Pharmacology
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• 제15권6호
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• pp.423-429
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• 2011

B13 analogues are being considered as therapeutic agents for cancer cells, since B13 is a ceramide analogue and inhibits ceramidase to promote apoptosis in cancer cells. B13 sulfonamides are assumed to have biological activity similar to B13, since they are made by bioisosterically substituting the carboxyl moiety of B13 with sulfone group. Twenty B13 sulfonamides were evaluated for their in vitro cytotoxicities against human colon cancer HT-29 and lung cancer A549 cell lines using MTT assays. Replacement of the amide group with a sulfonamide group increased cytotoxicity in both cancer cell lines. The sulfonamides with long alkyl chains exhibited activities two to three times more potent than that of B13 and compound (15) had the most potent activity with $IC_{50}$ values of 27 and $28.7{\mu}M$ for HT-29 and A549, respectively. The comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were used to carry out QSAR molecular modeling of these compounds. The predictive CoMSIA models for HT-29 and A549 gave cross-validated q2 values of 0.703 and 0.830, respectively. From graphical analysis of these models, we suppose that the stereochemistry of 1,3-propandiol is not important for activity and that introduction of a sulfonamide group and long alkyl chains into B13 can increase cytotoxicity.