Sulphasomizole (5-p-Aminobenzenesulphonamido-3-Methylisothiazole): A New Antibacterial Sulphonamide

Adams, Alexandra; Freeman, W. A.; Holland, Angélique; Hossack, D. J. N.; Inglis, J.M.; Parkinson, Jonathan; Reading, H. W.; Rivett, K.F.; Slack, Robert J.; Sutherland, R.; Wien, R.

doi:10.1038/186221a0

Cited by 23 publications

(10 citation statements)

References 2 publications

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“…It is likely that the organisms making N-S compounds are using them as broad-spectrum toxins, similar to other molecules that are highly reactive biocides, such as cyanogen bromide, superoxide, oxirane derivatives, and others (Drahl et al, 2005;Gersch et al, 2012;Vanelslander et al, 2012). The broad biocidal properties of natural N-S compounds are also mirrored by biological activities of many synthetic N-S compounds that are commonly used in many industries, for example as wood preservatives, fungicides in paints, acaricides, insecticides, pesticides, herbicides, and antibiotics in medicine (Adams et al, 1960;Kalgutkar et al, 2010;Bektas and Eulgem, 2014;Kalogirou and Koutentis, 2014) (Table 1). Thus, our statistical observation on toxicity of N-S compounds supports the inherent incompatibility of N-S bond chemistry with life.…”

Section: Possible Reasons For the Exclusion Of Thiol-mentioning

confidence: 99%

An Apparent Binary Choice in Biochemistry: Mutual Reactivity Implies Life Chooses Thiols or Nitrogen-Sulfur Bonds, but Not Both

2019

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A fundamental goal of biology is to understand the rules behind life's use of chemical space. Established work focuses on why life uses the chemistry that it does. Given the enormous scope of possible chemical space, we postulate that it is equally important to ask why life largely avoids certain areas of chemical space. The nitrogen-sulfur bond is a prime example, as it rarely appears in natural molecules, despite the very rich N-S bond chemistry applied in various branches of industry (e.g., industrial materials, agrochemicals, pharmaceuticals). We find that, out of more than 200,000 known, unique compounds made by life, only about 100 contain N-S bonds. Furthermore, the limited number of N-S bond-containing molecules that life produces appears to fall into a few very distinctive structural groups. One may think that industrial processes are unrelated to biochemistry because of a greater possibility of solvents, catalysts, and temperatures available to industry than to the cellular environment. However, the fact that life does rarely make N-S bonds, from the plentiful precursors available, and has evolved the ability to do so independently several times, suggests that the restriction on life's use of N-S chemistry is not in its synthesis. We present a hypothesis to explain life's extremely limited usage of the N-S bond: that the N-S bond chemistry is incompatible with essential segments of biochemistry, specifically with thiols. We support our hypothesis by (1) a quantitative analysis of the occurrence of N-S bond-containing natural products and (2) reactivity experiments between selected N-S compounds and key biological molecules. This work provides an example of a reason why life nearly excludes a distinct region of chemical space. Combined with future examples, this potentially new field of research may provide fresh insight into life's evolution through chemical space and its origin and early evolution.

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Section: Possible Reasons For the Exclusion Of Thiol-mentioning

confidence: 99%

An Apparent Binary Choice in Biochemistry: Mutual Reactivity Implies Life Chooses Thiols or Nitrogen-Sulfur Bonds, but Not Both

2019

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“…1). 4 Isothiazolonaphthoquinone, aulosirazole, isolated from blue-green algae exhibited tumor-selective cytotoxicity (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Neat synthesis of isothiazole compounds, and studies on their synthetic applications and photophysical properties

Bera

Patra²,

Azad³

et al. 2022

New J. Chem.

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“…1,2-Azoles are five-membered heterocycles containing at least one nitrogen atom and privileged structures widely found in pharmaceuticals 1 – 7 , pesticides 8 , and chiral catalysts 9 or ligands 10 , 11 (Fig. 1a ).…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach

et al. 2022

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Abstract1,2-Azoles are privileged structures in ligand/catalyst design and widely exist in many important natural products and drugs. In this report, two types of axially chiral 1,2-azoles (naphthyl-isothiazole S-oxides with a stereogenic sulfur center and atropoisomeric naphthyl pyrazoles) are synthesized via modified vinylidene ortho-quinone methide intermediates. Diverse products are acquired in satisfying yields and good to excellent enantioselectivities. The vinylidene ortho-quinone methide intermediates bearing two hetero atoms at 5-position have been demonstrated as a platform molecule for the atroposelective synthesis of axially chiral 1,2-azoles. This finding not only enrich our knowledge of vinylidene ortho-quinone methide chemistry but also provide the easy preparation method for diverse atropisomeric heterobiaryls that were inaccessible by existing methodologies. The obtained chiral naphthyl-isothiazole S-oxides and naphthyl-pyrazoles have demonstrated their potential application in further synthetic transformations and therapeutic agents.

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Sulphasomizole (5-p-Aminobenzenesulphonamido-3-Methylisothiazole): A New Antibacterial Sulphonamide

Cited by 23 publications

References 2 publications

An Apparent Binary Choice in Biochemistry: Mutual Reactivity Implies Life Chooses Thiols or Nitrogen-Sulfur Bonds, but Not Both

An Apparent Binary Choice in Biochemistry: Mutual Reactivity Implies Life Chooses Thiols or Nitrogen-Sulfur Bonds, but Not Both

Neat synthesis of isothiazole compounds, and studies on their synthetic applications and photophysical properties

Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach

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