New strategies to symmetric and unsymmetric cyclic sulfamide analogs of DMP 323: a ‘sulfur linchpin’/RCM approach

Jun, Jung Ho; Dougherty, Jack; Jiménez, M.; Hanson, Paul R.

doi:10.1016/j.tet.2003.04.001

Cited by 27 publications

(9 citation statements)

References 40 publications

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“…Subsequent dihydroxylation produced the cyclic sulfamide diol in 99% yield. 85 Unsymmetric sulfamides were also generated with high efficiency (Scheme 50). 84,85 RCM precursors were In 2003, a solution-phase pathway toward cyclic sulfamides using high-load soluble ROMP supports was developed (Scheme 51).…”

Section: Sulfamides R 2 N−so 2 −Nr′mentioning

confidence: 99%

“…85 Unsymmetric sulfamides were also generated with high efficiency (Scheme 50). 84,85 RCM precursors were In 2003, a solution-phase pathway toward cyclic sulfamides using high-load soluble ROMP supports was developed (Scheme 51). 87 The methodology revolves around a ring-opening metathesis polymerization phase trafficking (ROMPpt) strategy.…”

Section: Sulfamides R 2 N−so 2 −Nr′mentioning

confidence: 99%

“…In 2000, RCM strategies were developed to generate symmetric and unsymmetric cyclic sulfamides , related to the potent HIV-protease inhibitor DMP 323 developed at DuPont Merck . A route to several C 2 -symmetric sulfamides derived from amino esters is outlined in Scheme .…”

Section: 32 Sulfamides R2n−so2−nr‘2mentioning

confidence: 99%

“…In a newly related route, shown in Scheme , the robust nature of the sulfamide group is exemplified in a three-step protocol, converting each of the homotopic ester moieties in 49.1 to the terminal olefins residing in 49.2 that are armed for RCM. Metathesis with 5 mol % of B generated cyclic sulfamide 49.4 in 69% yield.…”

Section: 32 Sulfamides R2n−so2−nr‘2mentioning

confidence: 99%

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Synthesis of Phosphorus and Sulfur Heterocycles via Ring-Closing Olefin Metathesis

2004

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Section: Sulfamides R 2 N−so 2 −Nr′mentioning

confidence: 99%

Section: Sulfamides R 2 N−so 2 −Nr′mentioning

confidence: 99%

Section: 32 Sulfamides R2n−so2−nr‘2mentioning

confidence: 99%

Section: 32 Sulfamides R2n−so2−nr‘2mentioning

confidence: 99%

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Synthesis of Phosphorus and Sulfur Heterocycles via Ring-Closing Olefin Metathesis

2004

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“…We have devoted our efforts to the development of synthetic methods for the sulfur-containing small molecule compounds in various ways. − The synthesis of amino ester-derived C 2 -symmetric and unsymmetric sulfamides and further synthesis are described in Scheme . Amino esters are useful chiral auxiliary groups that are employed in medicinal chemistry synthesis and have been utilized in a wide range of areas such as peptide synthesis, asymmetric synthesis, and medicinal chemistry.…”

mentioning

confidence: 99%

Investigation on the Anticancer Activity of Symmetric and Unsymmetric Cyclic Sulfamides

Jun

Duscharla

Ummanni

et al. 2021

ACS Med. Chem. Lett.

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The sulfamide functional group has been extensively employed in organic synthesis to discover probes and drugs in various applications such as cancer, human immunodeficiency virus (HIV), virus, and diabetes. Herein, we describe the synthesis of 7membered symmetric and unsymmetric sulfamide compounds and their biological evaluation through the National Cancer Institute (NCI) panel of 60 human tumor cell lines (NCI-60) and the mechanism of action study. The results of a study from the NCI-60 cell line exhibited that many synthesized cyclic sulfamide compounds inhibited breast cancer (MDA-MB-468). The mechanism of action study of a representative compound 18 showed the inhibition of proliferation and apoptosis in A549 lung cancer cells.

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Olefin Ring‐Closing Metathesis

Yet

2016

Organic Reactions

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The olefin ring‐closing metathesis reaction catalyzed by ruthenium and molybdenum complexes has been employed in the syntheses of carbocycles, heterocycles, supramolecular compounds, and in tandem metathesis reactions. Chiral ruthenium and molybdenum catalysts have provided high enantiomeric and diastereomeric excesses in ring‐closing metathesis reactions. Many of the unsuccessful medium‐ and large‐sized ring formations which were unsuccessful by traditional methods, such as the intramolecular Wittig, Horner–Wadsworth–Emmons, and Julia–Kocienski reactions, can now be formed by olefin ring‐closing metathesis reactions. Ring‐closing metathesis has been a key step and sometimes the only successful method for the synthesis of numerous natural products and drug discovery targets. The objective of this chapter is to provide an updated, comprehensive coverage of the literature of the olefin ring‐closing metathesis reaction and related processes. Key mechanistic points are summarized.

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New strategies to symmetric and unsymmetric cyclic sulfamide analogs of DMP 323: a ‘sulfur linchpin’/RCM approach

Cited by 27 publications

References 40 publications

Synthesis of Phosphorus and Sulfur Heterocycles via Ring-Closing Olefin Metathesis

Synthesis of Phosphorus and Sulfur Heterocycles via Ring-Closing Olefin Metathesis

Investigation on the Anticancer Activity of Symmetric and Unsymmetric Cyclic Sulfamides

Olefin Ring‐Closing Metathesis

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