12-(((benzyloxy)carbonyl)amino)dodecanoic acid | 4272-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 12-(((benzyloxy)carbonyl)amino)dodecanoic acid
• 英文别名: 12-{[(Benzyloxy)carbonyl]amino}dodecanoic acid；12-(phenylmethoxycarbonylamino)dodecanoic acid
• CAS: 4272-07-5
• 化学式: C₂₀H₃₁NO₄
• 分子量: 349.47
• InChiKey: QENTWRVYFIAEFV-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  525.4±33.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  12-(((benzyloxy)carbonyl)amino)dodecanoic acid 在 palladium on activated charcoal 草酰氯 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙二醇甲醚 为溶剂， 反应 6.0h， 生成 N^α-(12-amino-1-dodecanoyl)-N^ε-lauroyl-L-lysine ethyl ester
  参考文献：
  名称：

  Supramolecular hydrogel formed by glucoheptonamide of l-lysine: simple preparation and excellent hydrogelation ability

  摘要：

  We describe the simple preparation of new L-lysine derivatives with a gluconic or glucoheptonic group, their hydrogelation properties, and the thermal and mechanical properties of the supramolecular hydrogels. The L-lysine derivatives with a gluconic group have no hydrogelation ability, while the L-lysine-glucoheptonamide derivatives functioned as hydrogelators. Their hydrogelation abilities increased with the decreasing length of the spacer between the L-lysine segment and the glucoheptonic group. The compound, which has no spacer, formed a supramolecular hydrogel at 0.05 wt% in pure water. The thermal stability and high mechanical strength of the supramolecular hydrogels based on this compound significantly depended on the aqueous solutions. Electron microscopy and FTIR studies demonstrated that the hydrogelators created a three-dimensional network through hydrogen bonding and hydrophobic interactions in the supramolecular hydrogel. In addition, it was found that hydrophobic interactions played an important role in the thermal stability of the supramolecular hydrogel. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.065
• 作为产物：
  描述：

  methyl 12-aminododecanoate 在 4-二甲氨基吡啶 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 12-(((benzyloxy)carbonyl)amino)dodecanoic acid
  参考文献：
  名称：

  1-O-(ω-氨基月桂基)-I(4,5)P2的多功能合成

  摘要：

  模型 1-O-(ω-氨基酰基)-IP2 衍生物、月桂基 4,5-二磷酸酯 31 的合成是按照通用且高产的方案实现的。用于此目的的灵活合成策略允许制备一系列其他有用的 IP、IP2 和 IP3 衍生物。鉴于 IPs 和 PIPs 在细胞生命中发挥的核心作用，这种类型的功能化肌醇衍生物的制备可能有助于相关蛋白质的分离和荧光定位。

  DOI：

  10.1002/ejoc.201200726

文献信息

• [EN] PDE4 INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND THERAPEUTIC APPLICATIONS<br/>[FR] INHIBITEURS DE PDE4, COMPOSITIONS PHARMACEUTIQUES ET APPLICATIONS THÉRAPEUTIQUES
  申请人：BIOTHERYX INC

  公开号：WO2021119571A1

  公开（公告）日：2021-06-17

  Provided herein are phosphodiesterase 4 (PDE4) inhibitors, e.g., a compound of Formula (I) or (II), and pharmaceutical compositions thereof. Also provided herein are methods of their use for treating, preventing, or ameliorating one or more symptoms of a disease, disorder, or condition associated with PDE4 malfunction.

  提供的是磷酸二酯酶4（PDE4）抑制剂，例如，公式（I）或（II）的化合物，以及它们的药物组合物。还提供了使用它们来治疗、预防或改善与PDE4功能障碍相关的一种或多种疾病、紊乱或症状的方法。
• Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes
  作者：Stuart J. Conway、James Gardiner、Simon J. A. Grove、Melloney K. Johns、Ze-Yi Lim、Gavin F. Painter、Diane E. J. E. Robinson、Christine Schieber、Jan W. Thuring、Leon S.-M. Wong、Meng-Xin Yin、Antony W. Burgess、Bruno Catimel、Phillip T. Hawkins、Nicholas T. Ktistakis、Leonard R. Stephens、Andrew B. Holmes

  DOI：10.1039/b913399b

  日期：——

  The synthesis of the complete family of phosphatidylinositol phosphate analogues (PIPs) from five key core intermediates A–E is described. These core compounds were obtained from myo-inositol orthoformate 1via regioselective DIBAL-H and trimethylaluminium-mediated cleavages and a resolution–protection process using camphor acetals 10. Coupling of cores A–E with phosphoramidites 34 and 38, derived from the requisite protected lipid side chains, afforded the fully-protected PIPs. Removal of the remaining protecting groups was achieved via hydrogenolysis using palladium black or palladium hydroxide on carbon in the presence of sodium bicarbonate to afford the complete family of dipalmitoyl- and amino-PIP analogues 42, 45, 50, 51, 58, 59, 67, 68, 76, 77, 82, 83, 92, 93, 99 and 100. Investigations using affinity probes incorporating these compounds have identified novel proteins involved in the PI3K intracellular signalling network and have allowed a comprehensive proteomic analysis of phosphoinositide interacting proteins.

  报道了从五个关键的核心中间体A-E合成完整的磷脂酰肌醇磷酸类似物（PIPs）家族的方法。这些核心化合物通过选择性DIBAL-H和三甲基铝介导的裂解以及使用樟脑乙缩醛的解析保护过程，从肌醇原甲酸1中获得。将核心A-E与从所需保护的脂质侧链衍生的磷酰胺34和38偶联，得到了完全保护的PIPs。通过使用钯黑或碳上的钯氢氧化物在碳酸氢钠存在下的氢解，去除了剩余的保护基团，得到了完整的二棕榈酰和氨基PIP类似物42、45、50、51、58、59、67、68、76、77、82、83、92、93、99和100。利用包含这些化合物的亲和探针进行的研究，鉴定了参与PI3K细胞内信号网络的新蛋白，并允许对磷脂酰肌醇相互作用蛋白进行全面的蛋白质组学分析。
• Synthesis and Structure-Activity Relationships of TAN-1511 Analogues as Potent Hematopoietic Agents.
  作者：Fumio ITOH、Yuji NISHIKIMI、Atsushi HASUOKA、Yoshio YOSHIOKA、Koichi YUKISHIGE、Seiichi TANIDA、Tetsuya AONO

  DOI：10.1248/cpb.46.255

  日期：——

  A series of TAN-1511 analogues bearing a non-peptide spacer in place of the Gly-Gly-Gly sequence in the peptide moiety was synthesized, and the effects of these compounds on the proliferation of bone marrow cells in culture and experimental leukocytopenia in mice were examined. The structure-activity relationships obtained were as follows. As the substituent at the 2-position of the 4-thiaheptanoic acid framework, an amino group, methyl group or hydrogen was preferable; as a spacer in place of the Gly-Gly-Gly sequence, a 4-aminobenzoyl or 4-aminomethylbenzoyl group was suitable; and as the fatty acids bonded to the 6, 7-dihydroxy groups, C16 fatty acid was best. Compounds 12f, 30d and 30i potently promoted the proliferation of bone marrow cells in culture and the restoration of leukocyte counts in a murine leukocytopenia model.

  合成了一系列TAN-1511类似物，这些类似物在肽部分中以非肽间隔物替代了Gly-Gly-Gly序列，并研究了这些化合物对体外骨髓细胞增殖和小鼠实验性白细胞减少症的影响。获得的结构-活性关系如下：作为4-硫代庚酸骨架2位的取代基，氨基、甲基或氢较为适宜；作为Gly-Gly-Gly序列的间隔物，4-氨基苯甲酰基或4-氨基甲基苯甲酰基较为合适；而与6,7-二羟基相连的脂肪酸中，C16脂肪酸最佳。化合物12f、30d和30i能显著促进体外骨髓细胞的增殖，并在小鼠白细胞减少模型中有效恢复白细胞计数。
• COMPOUND OR SALT THEREOF, NATURAL KILLER T CELL ACTIVATOR, AND PHARMACEUTICAL COMPOSITION
  申请人：KEIO UNIVERSITY

  公开号：US20200207798A1

  公开（公告）日：2020-07-02

  The invention provides a compound or a salt thereof capable of activating natural killer T cell, a natural killer T cell activating agent containing such a compound or a salt thereof, and a pharmaceutical composition. The compound of the invention is a compound represented by the following formula (1) or a salt thereof. It is preferable that total carbon number of the number of carbon atoms in the monovalent hydrocarbon group in R 1 in the formula (1) excluding a substitutent and the number of carbon atoms in the divalent hydrocarbon group in X 1 is 5 to 50. The natural killer T cell activating agent contains the aforementioned compound or a salt thereof. The pharmaceutical composition contains the aforementioned compound or a pharmacologically acceptable salt thereof.

  该发明提供了一种能够激活自然杀伤T细胞的化合物或其盐，包含这种化合物或其盐的自然杀伤T细胞激活剂，以及一种药物组合物。该发明的化合物是由以下式（1）表示的化合物或其盐。最好的情况是，在式（1）中R1中的单价碳氢化合物基中的碳原子数（不包括取代基）和X1中的双价碳氢化合物基中的碳原子数总和为5至50。自然杀伤T细胞激活剂含有上述化合物或其盐。药物组合物含有上述化合物或其药理学上可接受的盐。
• ALPHA-GALACTOSYLCERAMIDE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PREPARATION METHOD AND PHARMACEUTICAL COMPOSITION FOR THE IMMUNE ADJUVANT CONTAINING THE SAME AS AN ACTIVE INGREDIENT
  申请人：Kang Chang-Yuil

  公开号：US20100104590A1

  公开（公告）日：2010-04-29

  Disclosed are novel α-galactosylceramide derivatives, pharmaceutically acceptable salts thereof, preparation methods thereof, and pharmaceutical compositions for use in an immune adjuvant containing the same as an active ingredient. The derivatives, in which the amide moiety of α-GalCer is bioisosterically replaced with a triazole moiety, direct cytokine secretion toward IL-4 rather than IFN-γ and thus can be used as a therapeutic for autoimmune diseases regulated by IL-4, such as type 1 diabetes and multiple sclerosis.

  揭示了新颖的α-半乳糖鞘氨醇衍生物，其药用可接受的盐，其制备方法以及用于免疫佐剂的药物组合物，其中包含其作为活性成分。这些衍生物中，α-半乳糖鞘氨醇的酰胺基团被三唑基团生物异构地替代，将细胞因子分泌定向于IL-4而非IFN-γ，因此可以用作治疗由IL-4调节的自身免疫疾病，如1型糖尿病和多发性硬化症。