Category: benzofurans

CC-1065 Analogues Bearing Different DNA-Binding Subunits: Synthesis, Antitumor Activity, and Preliminary Toxicity Study was written by Wang, Yuqiang;Li, Lianfa;Ye, Wenqing;Tian, Zhiming;Jiang, Wei;Wang, Hong;Wright, Susan C.;Larrick, James W.. And the article was included in Journal of Medicinal Chemistry in 2003.Name: 5-Fluorobenzofuran-2-carboxylic acid This article mentions the following:

CC-1065 analogs bearing different DNA-binding subunits were synthesized. A terminal C5-NO₂ and -F moiety at the DNA-binding subunit increased the drug’s potency and antitumor efficacy. A C5-OCH₃ reduced the potency and antitumor efficacy. Compound (±)-I, bearing a trans double bond, had increased antitumor efficacy. A preliminary toxicity study indicated that terminal C5-OCH₃ and -acetamido moieties at the DNA-binding subunit caused delayed death in mice. In the experiment, the researchers used many compounds, for example, 5-Fluorobenzofuran-2-carboxylic acid (cas: 89197-62-6Name: 5-Fluorobenzofuran-2-carboxylic acid).

5-Fluorobenzofuran-2-carboxylic acid (cas: 89197-62-6) belongs to benzofurans derivatives. Benzofuran derivatives have shown many biological activities, including antifungal and antimicrobial properties, and acting as antagonists of H3 receptors and angiotensin II. Introduction of benzofurans in organic synthesis, particularly drug synthesis, involves generally the use of their metalated species as nucleophiles in addition reactions or in metal-catalysed cross-coupling reactions.Name: 5-Fluorobenzofuran-2-carboxylic acid

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Small molecule probes to quantify the functional fraction of a specific protein in a cell with minimal folding equilibrium shifts was written by Liu, Yu;Tan, Yun Lei;Zhang, Xin;Bhabha, Gira;Ekiert, Damian C.;Genereux, Joseph C.;Cho, Younhee;Kipnis, Yakov;Bjelic, Sinisa;Baker, David;Kelly, Jeffery W.. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2014.Application In Synthesis of 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate This article mentions the following:

Although much is known about protein folding in buffers, it remains unclear how the cellular protein homeostasis network functions as a system to partition client proteins between folded and functional, soluble and misfolded, and aggregated conformations. Herein, we develop small mol. folding probes that specifically react with the folded and functional fraction of the protein of interest, enabling fluorescence-based quantification of this fraction in cell lysate at a time point of interest. Importantly, these probes minimally perturb a protein’s folding equilibrium within cells during and after cell lysis, because sufficient cellular chaperone/chaperonin holdase activity is created by rapid ATP depletion during cell lysis. The folding probe strategy and the faithful quantification of a particular protein’s functional fraction are exemplified with retroaldolase, a de novo designed enzyme, and transthyretin, a nonenzyme protein. Our findings challenge the often invoked assumption that the soluble fraction of a client protein is fully folded in the cell. Moreover, our results reveal that the partitioning of destabilized retroaldolase and transthyretin mutants between the aforementioned conformational states is strongly influenced by cytosolic proteostasis network perturbations. Overall, our results suggest that applying a chem. folding probe strategy to other client proteins offers opportunities to reveal how the proteostasis network functions as a system to regulate the folding and function of individual client proteins in vivo. In the experiment, the researchers used many compounds, for example, 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate (cas: 92557-80-7Application In Synthesis of 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate).

2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate (cas: 92557-80-7) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.Application In Synthesis of 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Novel 2-arylbenzofuran dimers and polyisoprenylated flavanones from Sophora tonkinensis was written by Luo, Guoyong;Yang, Yun;Zhou, Min;Ye, Qi;Liu, Yan;Gu, Jian;Zhang, Guolin;Luo, Yinggang. And the article was included in Fitoterapia in 2014.Related Products of 6807-83-6 This article mentions the following:

Two novel 2-arylbenzofuran dimers, shandougenines A (1) and B (2), and two new polyisoprenylated flavanones 3 (shandougenine C) and 4 (shandougenine D) were isolated from the 95% EtOH extract of Sophora tonkinensis, together with 18 known compounds Their structures were determined on the basis of spectral data interpretation and by comparing the spectral data with that reported previously for known compounds Shandougenine A (1) is a unique dimeric 2-arylbenzofuran with a C-3-C-5”’ bond linkage. Shandougenine B (2) is the first naturally occurring dimeric 2-arylbenzofuran with a novel C-3-C-3” bond linkage. Compound 1 showed moderate DPPH free radical scavenging capacity, whereas 2 has stronger DPPH free radical and ABTS cation radical scavenging capacity than Vc. Compounds 12, 19, and 20 showed parallel DPPH free radical scavenging capacity with Vc. Compounds 1, 3, 4, 19, 20, and 22 have parallel ABTS cation radical scavenging capacity to Vc. Compounds 1, 3, 4, and 18 showed slightly stronger superoxide anion radical scavenging capacity than the known flavanone luteolin. The antioxidant activities of shandougenines A (1) and B (2) indicated that compounds 1 and 2 may represent novel scaffolds for the development of new antioxidants. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-2-(((6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[4′,5′:5,6]benzofuro[3,2-c]chromen-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 6807-83-6Related Products of 6807-83-6).

(2S,3R,4S,5S,6R)-2-(((6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[4′,5′:5,6]benzofuro[3,2-c]chromen-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 6807-83-6) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. In nature, benzofurans have occupied an important role among the plant phenols & several pharmacologically active compounds.Related Products of 6807-83-6

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

CC-1065 Analogues Bearing Different DNA-Binding Subunits: Synthesis, Antitumor Activity, and Preliminary Toxicity Study was written by Wang, Yuqiang;Li, Lianfa;Ye, Wenqing;Tian, Zhiming;Jiang, Wei;Wang, Hong;Wright, Susan C.;Larrick, James W.. And the article was included in Journal of Medicinal Chemistry in 2003.Name: 5-Fluorobenzofuran-2-carboxylic acid This article mentions the following:

CC-1065 analogs bearing different DNA-binding subunits were synthesized. A terminal C5-NO₂ and -F moiety at the DNA-binding subunit increased the drug’s potency and antitumor efficacy. A C5-OCH₃ reduced the potency and antitumor efficacy. Compound (±)-I, bearing a trans double bond, had increased antitumor efficacy. A preliminary toxicity study indicated that terminal C5-OCH₃ and -acetamido moieties at the DNA-binding subunit caused delayed death in mice. In the experiment, the researchers used many compounds, for example, 5-Fluorobenzofuran-2-carboxylic acid (cas: 89197-62-6Name: 5-Fluorobenzofuran-2-carboxylic acid).

5-Fluorobenzofuran-2-carboxylic acid (cas: 89197-62-6) belongs to benzofurans derivatives. Benzofuran derivatives have shown many biological activities, including antifungal and antimicrobial properties, and acting as antagonists of H3 receptors and angiotensin II. Introduction of benzofurans in organic synthesis, particularly drug synthesis, involves generally the use of their metalated species as nucleophiles in addition reactions or in metal-catalysed cross-coupling reactions.Name: 5-Fluorobenzofuran-2-carboxylic acid

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Small molecule probes to quantify the functional fraction of a specific protein in a cell with minimal folding equilibrium shifts was written by Liu, Yu;Tan, Yun Lei;Zhang, Xin;Bhabha, Gira;Ekiert, Damian C.;Genereux, Joseph C.;Cho, Younhee;Kipnis, Yakov;Bjelic, Sinisa;Baker, David;Kelly, Jeffery W.. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2014.Application In Synthesis of 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate This article mentions the following:

Although much is known about protein folding in buffers, it remains unclear how the cellular protein homeostasis network functions as a system to partition client proteins between folded and functional, soluble and misfolded, and aggregated conformations. Herein, we develop small mol. folding probes that specifically react with the folded and functional fraction of the protein of interest, enabling fluorescence-based quantification of this fraction in cell lysate at a time point of interest. Importantly, these probes minimally perturb a protein’s folding equilibrium within cells during and after cell lysis, because sufficient cellular chaperone/chaperonin holdase activity is created by rapid ATP depletion during cell lysis. The folding probe strategy and the faithful quantification of a particular protein’s functional fraction are exemplified with retroaldolase, a de novo designed enzyme, and transthyretin, a nonenzyme protein. Our findings challenge the often invoked assumption that the soluble fraction of a client protein is fully folded in the cell. Moreover, our results reveal that the partitioning of destabilized retroaldolase and transthyretin mutants between the aforementioned conformational states is strongly influenced by cytosolic proteostasis network perturbations. Overall, our results suggest that applying a chem. folding probe strategy to other client proteins offers opportunities to reveal how the proteostasis network functions as a system to regulate the folding and function of individual client proteins in vivo. In the experiment, the researchers used many compounds, for example, 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate (cas: 92557-80-7Application In Synthesis of 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate).

2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate (cas: 92557-80-7) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.Application In Synthesis of 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Novel 2-arylbenzofuran dimers and polyisoprenylated flavanones from Sophora tonkinensis was written by Luo, Guoyong;Yang, Yun;Zhou, Min;Ye, Qi;Liu, Yan;Gu, Jian;Zhang, Guolin;Luo, Yinggang. And the article was included in Fitoterapia in 2014.Related Products of 6807-83-6 This article mentions the following:

Two novel 2-arylbenzofuran dimers, shandougenines A (1) and B (2), and two new polyisoprenylated flavanones 3 (shandougenine C) and 4 (shandougenine D) were isolated from the 95% EtOH extract of Sophora tonkinensis, together with 18 known compounds Their structures were determined on the basis of spectral data interpretation and by comparing the spectral data with that reported previously for known compounds Shandougenine A (1) is a unique dimeric 2-arylbenzofuran with a C-3-C-5”’ bond linkage. Shandougenine B (2) is the first naturally occurring dimeric 2-arylbenzofuran with a novel C-3-C-3” bond linkage. Compound 1 showed moderate DPPH free radical scavenging capacity, whereas 2 has stronger DPPH free radical and ABTS cation radical scavenging capacity than Vc. Compounds 12, 19, and 20 showed parallel DPPH free radical scavenging capacity with Vc. Compounds 1, 3, 4, 19, 20, and 22 have parallel ABTS cation radical scavenging capacity to Vc. Compounds 1, 3, 4, and 18 showed slightly stronger superoxide anion radical scavenging capacity than the known flavanone luteolin. The antioxidant activities of shandougenines A (1) and B (2) indicated that compounds 1 and 2 may represent novel scaffolds for the development of new antioxidants. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-2-(((6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[4′,5′:5,6]benzofuro[3,2-c]chromen-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 6807-83-6Related Products of 6807-83-6).

(2S,3R,4S,5S,6R)-2-(((6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[4′,5′:5,6]benzofuro[3,2-c]chromen-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 6807-83-6) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. In nature, benzofurans have occupied an important role among the plant phenols & several pharmacologically active compounds.Related Products of 6807-83-6

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Mono- and dialdehyde of trehalose: new synthons to prepare trehalose bio-conjugates was written by Greco, Valentina;Sciuto, Sebastiano;Rizzarelli, Enrico. And the article was included in Organic & Biomolecular Chemistry in 2021.Category: benzofurans This article mentions the following:

Trehalose, a non-reducing disaccharide of glucose, is a natural bioactive and non-toxic sugar. It is found in many organisms that synthesize it when their cells are exposed to stress conditions. While not produced by mammalian cells, this disaccharide and also some of its derivatives have been shown to have a number of interesting properties that indicate their importance in the treatment of certain human diseases. Differentiating the two glucosyl moieties in the trehalose mol. has often been a synthetic challenge. We report here an easy way to obtain the mono-aldehyde of trehalose, as well as the relevant sym. dialdehyde. The reactivity of the aldehyde functionalities involved in the mol. structure of these synthons allows the easy preparation of the corresponding amino or carboxy derivatives of trehalose, as well the synthesis of some new trehalose conjugates useful for diagnostic or therapeutic purposes. In the experiment, the researchers used many compounds, for example, 5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 3326-34-9Category: benzofurans).

5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 3326-34-9) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Category: benzofurans

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Platinum-on-Carbon-Catalyzed Aqueous Oxidative Lactonization of Diols by Using Molecular Oxygen was written by Takakura, Ryoya;Ban, Kazuho;Sajiki, Hironao;Sawama, Yoshinari. And the article was included in Synlett in 2019.Related Products of 54120-64-8 This article mentions the following:

A lactonization of various diols e.g., I catalyzed by platinum on carbon (Pt/C) in water under an atm. of mol. oxygen was developed. Diols e.g., I were transformed into lactones e.g., II by the present oxidative lactonization method. In the experiment, the researchers used many compounds, for example, 5-Methylisobenzofuran-1(3H)-one (cas: 54120-64-8Related Products of 54120-64-8).

5-Methylisobenzofuran-1(3H)-one (cas: 54120-64-8) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.Related Products of 54120-64-8

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

An efficient synthesis of 4-substituted coumarin derivatives via a palladium-catalyzed Suzuki cross-coupling reaction was written by Rajale, Trideep;Sharma, Shikha;Stroud, Daniel A.;Unruh, Daniel K.;Miaou, Emily;Lai, Kimberly;Birney, David M.. And the article was included in Tetrahedron Letters in 2014.Synthetic Route of C8H5BF3KO This article mentions the following:

An efficient Pd-catalyzed Suzuki cross-coupling reaction of sterically crowded 4-chlorocoumarin derivatives with air- and moisture-stable potassium organotrifluoroborates is developed. This methodol. has been used to generate a series of novel alkyl, aryl, and vinyl substituted coumarin derivatives in good to excellent yields. The twisted conformation of the vinyl groups in the X-ray crystal structures of (2-oxo-4-vinyl-2H-chromen-3-yl)methyl acetate and (2-oxo-4-vinyl-2H-chromen-3-yl)methyl 2,2,2-trichloroacetimidate, along with the atropisomerism of 3-(hydroxymethyl)-4-(2-methoxyphenyl)-2H-chromen-2-one, are evidence of the steric crowding in these adducts. In the experiment, the researchers used many compounds, for example, Potassium benzofuran-2-yltrifluoroborate (cas: 929626-27-7Synthetic Route of C8H5BF3KO).

Potassium benzofuran-2-yltrifluoroborate (cas: 929626-27-7) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Synthetic Route of C8H5BF3KO

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

A UPLC-MS/MS method for in vivo and in vitro pharmacokinetic studies of psoralenoside, isopsoralenoside, psoralen and isopsoralen from Psoralea corylifolia extract was written by Wang, Yue-Fei;Liu, Ya-Nan;Xiong, Wen;Yan, Dong-Mei;Zhu, Yan;Gao, Xiu-Mei;Xu, Yan-Tong;Qi, Ai-Di. And the article was included in Journal of Ethnopharmacology in 2014.Synthetic Route of C17H18O9 This article mentions the following:

The dried fruit of Psoralea corylifolia L. has been used to prevent and treat vitiligo, osteoporosis, arthralgia and asthma in Traditional Chinese Medicine for some 1600 years. Psoralen (P), isopsoralen (IP), psoralenoside (PO) and isopsoralenoside (IPO) are the major coumarins and coumarin-related benzofuran glycosides in Psoraleae Fructus, which have been reported to show estrogen-like activity, osteoblastic proliferation accelerating activity, antitumor effects and antibacterial activity. The first aim of this study is to develop a rapid, sensitive and selective ultra performance liquid chromatog. tandem mass spectrometry (UPLC-MS/MS) approach for simultaneous determination of PO, IPO, P and IP in rat plasma and samples collected from in vitro incubation experiments The second aim is to investigate the pharmacokinetic properties of PO, IPO, P and IP after oral administration of Psoralea corylifolia extract (PCE) to rats. The third aim is to confirm the biotransformation of PO to P or IPO to IP under gastrointestinal conditions.A UPLC-MS/MS method with a C18 column and a mobile phase of methanol-0.1% aqueous formic acid was validated according to the criteria in FDA guidelines about bioanal. method, which was developed to investigate the pharmacokinetic behavior of PO, IPO, P and IP from PCE and the metabolic pathways of PO to P or IPO to IP.The criteria for establishment of a new UPLC-MS/MS method including selectivity, linearity, accuracy, precision, extraction recovery, matrix effect and stability were validated. This method was successfully applied to the quant. determination of PO, IPO, P and IP in biol. samples collected from both in vitro incubations and in vivo rat experiments After oral administration of PCE to rat, pharmacokinetic parameters of these four compounds indicated that in vivo biotransformation may occur between PO and P or IPO and IP. Purified benzofuran glycosides fraction (PBGF), containing only PO and IPO, was orally administered to rats to further confirm the biotransformation of PO to P or IPO to IP under gastrointestinal conditions. An in vitro incubation study elucidated that PO and IPO were metabolized to P and IP by intestinal microflora through de-glucosylation.This paper developed a rapid, sensitive and selective UPLC-MS/MS method for simultaneous determination of PO, IPO, P and IP from PCE in biol. samples, and investigated on their comprehensive in vivo and in vitro pharmacokinetic studies. These obtained results showed that the metabolism by intestinal bacteria plays an important role in pharmacol. effects of orally administered PCE. In the experiment, the researchers used many compounds, for example, (Z)-3-(6-(((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzofuran-5-yl)acrylic acid (cas: 905954-17-8Synthetic Route of C17H18O9).

(Z)-3-(6-(((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzofuran-5-yl)acrylic acid (cas: 905954-17-8) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.Synthetic Route of C17H18O9

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem