5-甲酰基异恶唑-3-甲酸甲酯 | 22667-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-甲酰基异恶唑-3-甲酸甲酯
• 中文别名: 5-甲酰基-3-异噁唑羧酸甲酯
• 英文名称: methyl 5-formylisoxazole-3-carboxylate
• 英文别名: 3-Carbomethoxy-5-Formylisoxazol；methyl 5-formyl-1,2-oxazole-3-carboxylate
• CAS: 22667-21-6
• 化学式: C₆H₅NO₄
• 分子量: 155.11
• InChiKey: RSOKVJLXFFQLLB-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 ºC
• 沸点：
  306 ºC
• 密度：
  1.348
• 闪点：
  139 ºC

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-甲酰基异恶唑-3-甲酸甲酯 在 lithium hydroxide 、 potassium tert-butylate 、 水 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 5-[(E)-2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propenyl]-isoxazole-3-carboxylic acid
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Heteroretinoids:  Induction of Apoptosis in the HL-60 Cell Line by a Novel Isoxazole-Containing Heteroretinoid

  摘要：

  In a search for retinoic acid receptor (RAR and RXR)-selective ligands, a series of isoxazole retinoids was synthesized and evaluated in vitro in transcriptional activation and competition binding assays for RARs and RXRs. In addition, these compounds were evaluated for their differentiating, cytotoxic, and apoptotic activities. In general, these derivatives showed scarcely any binding affinity and were nest active in the transcriptional assay. However, among these isoxazole derivatives, the cis-isomer 14b was identified as a potent inducer of apoptosis, and its activity was found to be 6.5 and 4 times superior than that of 13-cis- and 9-cis-retinoic acids, respectively. On the other hand, compound 13b, which has the trans stereochemistry at the double bond, was found not to be active in the apoptotic assay, but it was endowed with appreciable differentiating activity. Therefore, it seems that the different stereochemistry of the double bond may be associated with a different biological activity: potent apoptotic activity for the cis-isomer but differentiating activity for the traits structure. This biological behavior was found, at least in part, for the 9-cis- and 13-cis-retinoic acids with respect to the all-trans-retinoic acid. Thus, structure 14b could offer an interesting model for the design of new compounds endowed with apoptotic activity.

  DOI：

  10.1021/jm991059n
• 作为产物：
  描述：

  methyl 5-(tetrahydro-2H-pyran-2-yloxymethyl)isoxazole-3-carboxylate 在 Amberlite H-15 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 5-甲酰基异恶唑-3-甲酸甲酯
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Heteroretinoids:  Induction of Apoptosis in the HL-60 Cell Line by a Novel Isoxazole-Containing Heteroretinoid

  摘要：

  In a search for retinoic acid receptor (RAR and RXR)-selective ligands, a series of isoxazole retinoids was synthesized and evaluated in vitro in transcriptional activation and competition binding assays for RARs and RXRs. In addition, these compounds were evaluated for their differentiating, cytotoxic, and apoptotic activities. In general, these derivatives showed scarcely any binding affinity and were nest active in the transcriptional assay. However, among these isoxazole derivatives, the cis-isomer 14b was identified as a potent inducer of apoptosis, and its activity was found to be 6.5 and 4 times superior than that of 13-cis- and 9-cis-retinoic acids, respectively. On the other hand, compound 13b, which has the trans stereochemistry at the double bond, was found not to be active in the apoptotic assay, but it was endowed with appreciable differentiating activity. Therefore, it seems that the different stereochemistry of the double bond may be associated with a different biological activity: potent apoptotic activity for the cis-isomer but differentiating activity for the traits structure. This biological behavior was found, at least in part, for the 9-cis- and 13-cis-retinoic acids with respect to the all-trans-retinoic acid. Thus, structure 14b could offer an interesting model for the design of new compounds endowed with apoptotic activity.

  DOI：

  10.1021/jm991059n

文献信息

• COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY
  申请人：Chiesi Farmaceutici S.p.A.

  公开号：US20140163066A1

  公开（公告）日：2014-06-12

  Compounds of formula (I) defined herein act both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists and are useful for the prevention and/or treatment of broncho-obstructive or inflammatory diseases.

  本处定义的化合物（I）的化学式既作为肌肉收缩受体拮抗剂，又作为β2肾上腺素受体激动剂，可用于预防和/或治疗支气管阻塞或炎症性疾病。
• A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes
  作者：John Kallikat Augustine、Y. Arthoba Naik、Ashis Baran Mandal、Nagaraja Chowdappa、Vinuthan B. Praveen

  DOI：10.1016/j.tet.2007.11.030

  日期：2008.1

  Hydrolysis of geni-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f. (C) 2007 Elsevier Ltd. All rights reserved.
• Encoded Solid Phase Compound Library with Polynucleotide Based Barcoding
  申请人：The Scripps Research Institute

  公开号：US20200190507A1

  公开（公告）日：2020-06-18

  Provided herein are polynucleotide encoded chemical libraries comprising one or more bead members, wherein the beads comprise: a chemical moiety comprising a compound library member; a polynucleotide moiety comprising an oligonucleotide encoding the compound library member, and a barcode identifying the bead; and a linking moiety, linking the chemical moiety to the polynucleotide moiety. Also provided herein are methods of making and using the polynucleotide barcoded chemical libraries, as well as kits comprising the barcoded chemical library.
• US8980913B2
  申请人：——

  公开号：US8980913B2

  公开（公告）日：2015-03-17
• US9453013B2
  申请人：——

  公开号：US9453013B2

  公开（公告）日：2016-09-27