5-(1-hydroxynonylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione | 66696-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(1-hydroxynonylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione
• 英文别名: 5-(1-Hydroxynonylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 66696-82-0
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: HLJUTORYNBGDQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(1-hydroxynonylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 以 甲醇 为溶剂， 以118 mg的产率得到methyl 3-oxoundecanoate
  参考文献：
  名称：

  用于发现含有呋喃部分的天然产物的 Diels-Alder 探针

  摘要：

   抽象的 天然产物 (NP) 是新型药物的绝佳灵感来源，通常针对感兴趣的靶标表现出独特的生物活性。具体来说，含有呋喃部分的纳米粒子显示出对抗多种疾病的活性，包括真菌感染和癌症。然而，从细胞上清液中发现和分离这些小分子具有挑战性。本文描述的工作展示了一种分子探针的开发，该探针可以通过 [4 + 2] Diels-Alder 环加成共价修饰呋喃部分，使它们可以通过液相色谱-质谱 (LC-MS) 轻松识别。该分子探针与多种呋喃发生反应，设计有紫外线标签和质量标签，以便于识别。该探针已使用多种纯化呋喃进行了测试，包括天然产物、亚甲霉素呋喃 (MMF) 激素和 MMF 衍生物。此外，该分子探针已在各种链霉菌菌株的粗上清液中进行了测试，并且能够鉴定 MMF。 Beilstein J. Org. Chem. 2024, 20, 1001–1010. doi:10.3762/bjoc.20.88

  DOI：

  10.3762/bjoc.20.88
• 作为产物：
  描述：

  壬酸 以97%的产率得到5-(1-hydroxynonylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione
  参考文献：
  名称：

  WO2008/54290

  摘要：

  公开号：

文献信息

• Synthetic libraries of tyrosine-derived bacterial metabolites
  作者：Savvas N. Georgiades、Jon Clardy

  DOI：10.1016/j.bmcl.2007.10.058

  日期：2008.5

  The preparation of a collection of 131 small molecules, reminiscent of families of long chain N-acyl tyrosines, enamides and enol esters that have been isolated from heterologous expression of environmental DNA (eDNA) in Escherichia coli, is reported. The synthetic libraries of N-acyl tyrosines and their 3-keto counterparts were prepared via solid-phase routes, whereas the enamides and enol esters

  据报道，制备了 131 个小分子的集合，让人联想到长链 N-酰基酪氨酸、烯酰胺和烯醇酯家族，这些分子是从大肠杆菌环境 DNA (eDNA) 的异源表达中分离出来的。N-酰基酪氨酸及其3-酮对应物的合成库是通过固相途径制备的，而烯酰胺和烯醇酯是在溶液相中合成的。
• Isolation of the antibiotic pseudopyronine B and SAR evaluation of C3/C6 alkyl analogs
  作者：Leah M. Bouthillette、Catherine A. Darcey、Tess E. Handy、Sarah C. Seaton、Amanda L. Wolfe

  DOI：10.1016/j.bmcl.2017.04.067

  日期：2017.6

  for antibacterial activity against Gram-positive and Gram-negative bacteria. We found a direct relationship between antibacterial activity and C3/C6 alkyl chain length. For inhibition of Gram-positive bacteria, alkyl chain lengths between 6 and 7 carbons were found to be the most active (IC50=0.04-3.8µg/mL) whereas short alkyl chain analogs showed modest activity against Gram-negative bacteria (IC50=223-304µg/mL)

  天然产物是具有抗菌活性的结构多样的化合物的丰富来源，可用于开发新型有效的抗生素。一类这样的天然产物是假吡喃酮。在这里，我们介绍了从北卡罗莱纳州西部花园土壤中发现的假单胞菌属物种中分离出假吡喃酮B（2），以及对天然产物的C3和C6烷基类似物对革兰氏阳性和革兰氏阴性细菌的抗菌活性的SAR评估。我们发现抗菌活性和C3 / C6烷基链长之间存在直接关系。为了抑制革兰氏阳性菌，发现6​​至7个碳原子之间的烷基链长度最活跃（IC50 = 0.04-3.8µg / mL），而短链烷基类似物对革兰氏阴性菌的活性中等（IC50 = 223） -304µg / mL）。
• New Compounds
  申请人：Almqvist Fredrik

  公开号：US20080139607A1

  公开（公告）日：2008-06-12

  The present invention relates to new compounds of formula (I), (II), or (III) wherein R 1 , R 2 , R 3 , R 4 , R 5 and W are as defined herein, and methods of using the compounds to inhibit PAI-1 and to treat PAI-1 related disorders.

  本发明涉及式(I)、(II)或(III)的新化合物，其中R1、R2、R3、R4、R5和W的定义如本文所述，并且使用这些化合物抑制PAI-1和治疗PAI-1相关疾病的方法。
• Synthetic Analogues of the Bacterial Signal (Quorum Sensing) Molecule <i>N</i>-(3-Oxododecanoyl)-<scp>l</scp>-homoserine Lactone as Immune Modulators
  作者：Siri Ram Chhabra、Chris Harty、Doreen S. W. Hooi、Mavis Daykin、Paul Williams、Gary Telford、David I. Pritchard、Barrie W. Bycroft

  DOI：10.1021/jm020909n

  日期：2003.1.1

  Comparative immune modulatory activity for a range of synthetic analogues of a Pseudomonas aeruginosa signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone (3O, C-12-HSL), is described. Twenty-four single or combination systematic alterations of the structural components of 3O, C12-HSL were introduced as described. Given the already defined immunological profile of the parent compound, 3O, C12-HSL, these compounds were assayed for their ability to inhibit murine and human leucocyte proliferation and TNF-alpha secretion by lipopolysaccharide (LPS) stimulated human leucocytes in order to provide an initial structure-activity profile. From IC50 values obtained with a murine splenocyte proliferation assay, it is apparent that acylated L-homoserine lactones with an 11-13 C side chain containing either a 3-oxo or a 3-hydroxy group are optimal structures for immune suppressive activity. These derivatives of 3O, C-12-HSL with monounsaturation and/or a terminal nonpolar substituent on the side chain were also potent immune suppressive agents. However, structures lacking the homoserine lactone ring, structures lacking the L-configuration at the chiral center, and those with polar substituents were essentially devoid of activity. The ability of compounds selected from the optimal activity range to modulate mitogen-driven human peripheral blood mononuclear cell proliferation and LPS-induced TNF-alpha secretion indicates the suitability of these compounds for further investigation in relation to their molecular mechanisms of action in TNF-alpha driven immunological diseases, particularly autoimmune diseases such as psoriasis, rheumatoid arthritis, and type 1 (autoimmune) diabetes.
• Novel amides and esters prodrugs of olmesartan: Synthesis, bioconversion, and pharmacokinetic evaluation
  作者：Jin-Hun Park、Jeong-Soo Chang、Mohammed I. El-Gamal、Won-Kyoung Choi、Woong San Lee、Hye Jin Chung、Hyun-Il Kim、Young-Jin Cho、Bong Sang Lee、Hong-Ryeol Jeon、Yong Sup Lee、Young Wook Choi、Jaehwi Lee、Chang-Hyun Oh

  DOI：10.1016/j.bmcl.2010.07.089

  日期：2010.10

  Synthesis of novel amides and esters prodrugs of olmesartan is described. Their in vitro stability in rat plasma was tested. The results showed that the ester derivative IIa with n-octyl substituted dioxolone moiety was rapidly converted into olmesartan within 30 min. The pharmacokinetic parameters of IIa were studied and compared with those of olmesartan medoxomil. Compound IIa is proposed to be a promising prodrug of olmesartan. (C) 2010 Published by Elsevier Ltd.