Name: N-(2-Oxotetrahydrofuran-3-yl)butyramide
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

N-Butyrylhomoserine lactone; N-Butanoyl-DL-homoserine lactone; N-(2-oxooxolan-3-yl)butanamide; N-Butyryl-DL-homoserine lactone

IUPAC Name

N-(2-oxooxolan-3-yl)butanamide

Canonical SMILES

CCCC(=O)NC1CCOC1=O

InChI

InChI=1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)

InChIKey

VFFNZZXXTGXBOG-UHFFFAOYSA-N

Density

1.1±0.1 g/cm3

Solubility

Soluble in Chloroform

Appearance

White to Faint Beige Powder or Crystals

Boiling Point

428.1±34.0°C at 760 mmHg

N-(2-Oxotetrahydrofuran-3-yl)butyramide is a unique chemical compound with a tetrahydrofuran (THF) ring system attached to a butyramide group. This structure imparts interesting bioactive properties to the compound, making it an attractive candidate in medicinal chemistry and drug development. The THF ring system is known for its ability to interact with various enzymes and receptors, while the butyramide moiety can potentially engage in important biological interactions. As a result, this compound has promising applications in fields such as enzyme inhibition, cancer therapy, and drug discovery.

One of the most significant applications of N-(2-Oxotetrahydrofuran-3-yl)butyramide is in the development of enzyme inhibitors. The tetrahydrofuran ring is a versatile pharmacophore that can mimic natural substrates or transition states of enzymes, making it an effective scaffold for the design of enzyme inhibitors. This compound could be used to inhibit key enzymes involved in cellular processes, such as kinases, proteases, or metabolic enzymes. By selectively targeting these enzymes, N-(2-Oxotetrahydrofuran-3-yl)butyramide has the potential to modulate various biological pathways, including those involved in cancer, inflammation, and metabolic disorders. Enzyme inhibition could lead to therapeutic benefits in diseases characterized by overactive or dysregulated enzyme activity.

In cancer therapy, N-(2-Oxotetrahydrofuran-3-yl)butyramide may be valuable for targeting cancer cell growth and proliferation. The compound’s structure suggests that it may interact with molecular targets that regulate cell cycle progression or apoptosis. The ability to inhibit enzymes involved in these processes could disrupt tumor cell growth and enhance the effectiveness of existing cancer treatments. Additionally, the compound's specificity could reduce the side effects typically associated with conventional chemotherapy. By offering a targeted approach, N-(2-Oxotetrahydrofuran-3-yl)butyramide could potentially improve the precision and safety of cancer therapies, particularly in treating solid tumors that are difficult to target with current treatments.

Another promising application of this compound is in drug delivery systems. The tetrahydrofuran ring is often used in drug design to enhance solubility and bioavailability, making N-(2-Oxotetrahydrofuran-3-yl)butyramide a suitable candidate for incorporation into drug delivery formulations. Its ability to interact with biological membranes could help improve the compound's ability to cross cell barriers, ensuring better delivery of therapeutic agents. When conjugated with other bioactive molecules, N-(2-Oxotetrahydrofuran-3-yl)butyramide could serve as a linker in prodrug systems, allowing for the controlled release of active pharmaceutical ingredients at the desired site of action, reducing toxicity and enhancing treatment efficacy.

Finally, N-(2-Oxotetrahydrofuran-3-yl)butyramide can play a key role in high-throughput screening and drug discovery. Its unique structure and potential for enzyme modulation make it a valuable tool for screening libraries of small molecules for therapeutic activity. Researchers can use this compound as a lead molecule to identify new drug candidates for various diseases, particularly those related to enzyme dysregulation. In combination with advanced screening techniques, such as computational modeling and structure-activity relationship studies, this compound could lead to the discovery of novel therapeutic agents that target previously untapped biological pathways.

1. Occurrence of diversified N-acyl homoserine lactone mediated biofilm-forming bacteria in rice rhizoplane

Balachandar Dananjeyan, Viveka Balasundararajan J Basic Microbiol . 2019 Oct;59(10):1031-1039. doi: 10.1002/jobm.201900202.

Quorum sensing (QS)-mediated biofilm-forming rhizobacteria are indispensable due to their competitiveness in the crop rhizosphere. In the present work, we have reported on the occurrence of diversified bacterial species capable of producing N-acyl homoserine lactone (AHL) as the QS signal in the roots of a rice plant grown under field conditions. The AHL-producing bacteria were directly isolated from the rice root by the biosensor reporter (Chromobacterium violaceum CV026) overlay method and characterized for biofilm production by the microtiter plate method. A total of 48 QS-positive bacterial isolates were purified from different aged (7, 20, 24, 26, and 36 days) rice seedlings. The in vitro biofilm production and genetic diversity as revealed by BOX-PCR fingerprinting showed high variability among the isolates. Most of the best biofilm-forming isolates produced a N-butyryl dl-homoserine lactone (a C4-AHL type) signal in the medium. The 16S ribosomal RNA (rRNA) gene sequence of these putative elite isolates identified that they were close to Aeromonas hydrophila (QS7-4; QS36-2), A. enteropelongenes (QS20-8), A. veronii (QS36-3), Enterobacter sp. (QS20-11), Klebsiella pneumoniae (QS24-6), Kosakonia cowanii (QS24-21), Providentia rettigeri (QS24-2), Sphingomonas aquatilis (QS24-17), and Pseudomonas sihuiensis (QS24-20). These strains profusely colonized the rice root upon inoculation and formed biofilms on the surface of the root under gnotobiotic conditions. Developing inoculants from these strains would ensure competitive colonization on the rhizoplane of the crop through their biofilm and thereby improve plant growth and health.

2. Specific quorum sensing molecules of ammonia oxidizers and their role during ammonium metabolism in Zhalong wetland, China

Yupeng Zhang, Fengqin Liu, Hong Liang, Dawen Gao Sci Total Environ . 2019 May 20;666:1106-1113. doi: 10.1016/j.scitotenv.2019.02.261.

The primary challenge of ammonia-oxidizing archaea (AOA) and ammonia-oxidizing bacteria (AOB) surviving in wetlands are the rapid and unpredictable environmental changes. To adapt to a fluctuant environment, ammonia oxidizers have to communicate with each other via acyl-homoserine lactones (AHLs). In this study, AOA and AOB in the soil samples taken from Zhalong wetland were incubated. Dynamics of AHLs during the incubation of ammonia oxidizers were measured. Then, the specific AHLs of AOA and AOB were identified, respectively. The results showed that AOA secreted N-butyryl-dl-homoserine lactone (C4-HSL) and N-octanoyl-l-homoserine lactone (C8-HSL) to cope with nitrite accumulation, while they secreted N-(3-oxododecanoyl)-dl-homoserine lactone (OXOC12-HSL) to regulate their ammonium metabolism activity. AOB secreted N-hexanoyl-dl-homoserine lactone (C6-HSL), N-dodecanoyl-l-homoserine lactone (C12-HSL), N-tetradecanoyl-dl-homoserine lactone (C14-HSL) and N-(3-oxododecanoyl)-tetradecanoyl-dl-homoserine lactone (OXOC14-HSL) only to enhance the metabolism activity. The dominant AOA belonged to the Nitrososphaera lineage, while the dominant AOB grouped into the Nitrosomonas lineage. The AHLs receptor homologs were identified in both AOA and AOB, which confirmed that AOA and AOB had the QS system. The present work was the first study that elucidated the QS system of AOA and AOB in multidimensional, and confirmed the role of QS system in ammonia oxidizers' metabolism.

3. Response of Arabidopsis thaliana to N-hexanoyl-DL-homoserine-lactone, a bacterial quorum sensing molecule produced in the rhizosphere

Philippe Schmitt-Kopplin, Jana Kottova, Eva Zazimalova, Ilona Klein, Anton Hartmann, Uta von Rad, Petre I Dobrev, Jörg Durner, Agnes Fekete Planta . 2008 Dec;229(1):73-85. doi: 10.1007/s00425-008-0811-4.

The bacterial quorum sensing signals N-acyl-L: -homoserine lactones enable bacterial cells to regulate gene expression depending on population density, in order to undertake collective actions such as the infection of host cells. Only little is known about the molecular ways of plants reacting to these bacterial signals. In this study we show that the contact of Arabidopsis thaliana roots with N-hexanoyl-DL: -homoserine-lactone (C6-HSL) resulted in distinct transcriptional changes in roots and shoots, respectively. Interestingly, unlike most other bacterial signals, C6-HSL influenced only a few defense-related transcripts. Instead, several genes associated with cell growth as well as genes regulated by growth hormones showed changes in their expression after C6-HSL treatment. C6-HSL did not induce plant systemic resistance against Pseudomonas syringae. The inoculation of roots with different types of AHLs led predominantly for short chain N-butyryl-DL: -homoserine lactone and C6-HSL to root elongation. Determination of plant hormone concentrations in root and shoot tissues supported alterations of auxin to cytokinin ratio. Finally, we provide evidence that Arabidopsis takes up bacterial C6-HSL and allows systemic distribution throughout the plant. In sum, the bacterial quorum sensing signal C6-HSL does induce transcriptional changes in Arabidopsis and may contribute to tuning plant growth to the microbial composition of the rhizosphere.