3,5-双(羟甲基)苯甲酸甲酯 | 193953-02-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,5-双(羟甲基)苯甲酸甲酯
• 中文别名: 3,5-双羟甲基苯甲酸甲酯
• 英文名称: methyl 3,5-bis(hydroxymethyl)benzoate
• CAS: 193953-02-5
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: PDCYWPCWFFWHPP-UHFFFAOYSA-N

物化性质

• 熔点：
  105 °C
• 沸点：
  389.3±42.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3,5-双(羟甲基)苯甲酸甲酯 在 三溴化磷 作用下， 以 四氯化碳 为溶剂， 生成 5-methoxycarbonyl-m-xylylene bisphosphonic acid tetramethyl ester
  参考文献：
  名称：

  Efficient synthesis of water-soluble, phosphonate-terminated polyester dendrimers

  摘要：

  Simple and effective syntheses of novel, water-soluble, phosphonate-terminated polyester dendrimers varying in size and structure are described. These macromolecular compounds, consisting of thiophosphoric and 1,3,5-benzenetricarboxylic ester building blocks may find potential applications in health sciences as microbicides and/or as useful macromolecular models for functional coatings of superparamagnetic iron oxides (SPIOs) nanoparticles intended for use in hyperthermal therapy and magnetic resonance imaging (MRI). The dendrimers, possessing free phosphonate functional groups on the surface, were prepared in high yields from previously synthesized phosphorus-based substrates with 3,5-bis (dimethoxyphosphonyl)-methylibenzoic acid (4), being an essential precursor of the dendrimer polyanionic surface. In addition, an interesting example of virtual coupling between remote nuclei in the C-13 NMR spectrum of bisphosphonate monomer 3 was observed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.035
• 作为产物：
  描述：

  5-methoxycarbonyl-benzene-1,3-dicarboxylic acid 在 硼烷二甲硫醚络合物 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 以80%的产率得到3,5-双(羟甲基)苯甲酸甲酯
  参考文献：
  名称：

  新型水溶性聚阴离子树状聚合物—磷酸和1,3,5-苯三羧酸衍生物

  摘要：

  描述了简单，非常有效并且具有一般性的一些方面，其具有不同尺寸，极性和挠性的水溶性聚阴离子树枝状聚酯的合成。这些由磷酸酯或硫代磷酸酯单元和1,3,5-苯三羧酸结构单元组成的大分子化合物可能会作为药物使用。合成的标题聚阴离子树状聚合物在表面具有带电的羧基官能团，并以高收率从先前制备的一系列新的磷基树状多元醇中获得。该项目中使用的关键单体是1,3,5-苯三甲酸二苄酯和1,3,5-苯三甲酸双（4-甲氧基苄基）酯。两者都作为树枝状聚阴离子表面的基本前体。

  DOI：

  10.1016/j.tet.2012.09.094

文献信息

• Synthesis of Monodisperse Macromolecular Bicyclic and dendritic compounds from (R)-3-hydroxybutanoic acid and benzene-1,3,5-tricarboxylic acid and analysis by fragmenting MALDI-TOF mass spectroscopy
  作者：Dieter Seebach、Guide F. Herrmann、Urs D. Lengweiler、Walter Amrein

  DOI：10.1002/hlca.19970800402

  日期：1997.6.30

  elemental analysis. Especially important is the analysis by mass spectrometry with the MALDI-TOF technique (Fig. 2), proving that the products are monodisperse; application of a new variation of this MS method (post source decay = PSD or fragment analysis by structural time of flight = FASTTM) allows for the observation of metastable fragment ions and, thus, is a tool for structural oligomer analysis (Fig

  如前所示，低聚和聚（β-羟基链烷酸酯）很容易形成具有ca的层状微晶。50-Å的厚度，对应于16个单元的链长（图1）。具有单分散的模型化合物，我们现在已经制备双环衍生物与三个平行（27 - 29）或两个平行和反平行链（68 - 70）由最多至16 3-羟基丁酸（3-HB）单元。我们还制备树枝状化合物（71 - 75，82 - 85）含有不可能被布置为在低聚（3-HB）链薄片; 支链单元由均苯三酸（＝苯-1,3,5-三羧酸）制备。到目前为止，没有一个准备好的样品能够形成晶体或包含适合单晶或粉末衍射X射线分析的晶畴。的末端脱保护的树枝状聚合物（74，75，和85）是多阴离子（最多12个CO 2 H基团）和可生物降解的。通过IR，1 H-和13 C-NMR，[α] D和元素分析已充分表征了大分子HB衍生物（分子量高达10150 Da）。尤其重要的是使用MALDI-TOF技术进行的质谱分析（图2），
• [EN] CYTOTOXIC BIS-BENZODIAZEPINE DERIVATIVES AND CONJUGATES THEREOF WITH CELL-BINDING AGENTS FOR INHIBITING ABNORMAL CELL GROWTH OR FOR TREATING PROLIFERATIVE DISEASES<br/>[FR] DÉRIVÉS DE BIS-BENZODIAZÉPINE CYTOTOXIQUES ET LEURS CONJUGUÉS AVEC DES AGENTS DE LIAISON À UNE CELLULE POUR INHIBER LA CROISSANCE CELLULAIRE ANORMALE OU POUR TRAITER DES MALADIES PROLIFÉRATIVES
  申请人：IMMUNOGEN INC

  公开号：WO2020205564A1

  公开（公告）日：2020-10-08

  The invention relates to benzodiazepine derivatives with antiproliferative activity and more specifically to benzodiazepine compounds of formulae (I), (II), (TI) and (T2). The invention also provides conjugates of the benzodiazepine compounds linked to a cell-binding agent. The invention further provides compositions and methods for inhibiting abnormal cell growth or treating a proliferative disorder in a mammal using the compounds or conjugates of the invention.

  这项发明涉及具有抗增殖活性的苯二氮䓬啶衍生物，更具体地涉及具有式(I)、(II)、(TI)和(T2)的苯二氮䓬啶化合物。该发明还提供了与细胞结合剂连接的苯二氮䓬啶化合物的结合物。该发明还提供了使用该发明的化合物或结合物抑制异常细胞生长或治疗哺乳动物增殖性疾病的组合物和方法。
• A comparison of X-ray crystal structures including methyl 3,5-bis(hydroxymethyl)benzoate, its phenylethynyl extended derivative in polymorphous forms and the corresponding carboxylic acids
  作者：Felix Katzsch、Diana Eißmann、Edwin Weber

  DOI：10.1007/s11224-011-9858-0

  日期：2012.2

  Considering the specific supramolecular synthon design of carboxylic acid and alcoholic hydroxyl groups in the field of crystal engineering, we compared the solid state structures of particular benzoates and corresponding acids 1–4 both in the non-spacered (1, 2) and spacered (3, 4) forms. Based on the single crystal X-ray study, there is only a slight influence of the phenylacetylene spacer with regard to the layer lattice arrangement of the benzoates while referring to the benzoic acid analogues the addition of the spacer gives rise to a modification of the lattice from a layer to a tape structure. Dependent on the crystallization conditions, two crystalline polymorphs of compound 3 (3a, 3b) were obtained and discussed regarding their structural differences.

  考虑到晶体工程领域中羧酸和醇羟基特定超分子单体设计，我们比较了特定苯甲酸盐及其对应酸1-4在无间隔（1, 2）和有间隔（3, 4）形式中的固态结构。根据单晶X射线研究，苯甲酸盐的层状晶格排列在加入苯乙炔间隔基时仅有轻微影响，而参照苯甲酸类似物，间隔基的加入导致晶格结构从层状转变为带状。根据结晶条件，化合物3获得了两种晶型多晶型物（3a, 3b），并讨论了它们在结构上的差异。
• [EN] TRICYCLIC DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, THEIR PREPARATIONS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] DERIVES TRICYCLIQUES OU SELS PHARMACEUTIQUEMENT ACCEPTABLES DE CES DERIVES, LEURS PREPARATIONS ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：JE IL PHARMACEUTICAL CO LTD

  公开号：WO2004113281A1

  公开（公告）日：2004-12-29

  The present invention relates to tricyclic derivatives or pharmaceutically acceptable salts thereof, their preparations and pharmaceutical compositions containing them. More precisely, the present invention relates to tricyclic derivatives as colchicine derivatives, pharmaceutically acceptable salts thereof, their preparations and pharmaceutical compositions containing them. Tricyclic derivatives of the present invention show very powerful cytotoxicity to cancer cell lines but were much less toxic than colchicine or taxol, confirmed through animal toxicity test. Tricyclic derivatives of the invention also decrease the volume and weight of a tumor and have a strong angiogenesis inhibiting activity in HUVEC cells. Thus, tricyclic derivatives of the present invention can effectively be used as an anticancer agent, anti-proliferation agent and an angiogenesis inhibitor.

  本发明涉及三环衍生物或其药用盐，其制备以及含有它们的药物组合物。更准确地说，本发明涉及三环衍生物作为秋水仙碱衍生物，其药用盐，其制备以及含有它们的药物组合物。本发明的三环衍生物对癌细胞系表现出非常强大的细胞毒性，但比秋水仙碱或紫杉醇毒性要小得多，经动物毒性试验证实。本发明的三环衍生物还可以减小肿瘤的体积和重量，并且在HUVEC细胞中具有强大的抑制血管生成活性。因此，本发明的三环衍生物可以有效地用作抗癌剂、抗增殖剂和血管生成抑制剂。
• Study on the structure-activity relationship of dihydroartemisinin derivatives: Discovery, synthesis, and biological evaluation of dihydroartemisinin-bile acid conjugates as potential anticancer agents
  作者：Xiaosu Zou、Chang Liu、Congcong Li、Rong Fu、Wei Xu、Hongzhu Bian、Xun Dong、Xiaozhen Zhao、Zhenye Xu、Jinghua Zhang、Zhengwu Shen

  DOI：10.1016/j.ejmech.2021.113754

  日期：2021.12

  A series of dihydroartemisinin derivatives was synthesized, and their anti-proliferation activity against cancer cells was evaluated. Structure-activity relationship studies led to the discovery of dihydroartemisinin-bile acid conjugates that exhibit broad-spectrum anti-proliferation activities. Among them, the dihydroartemisinin-ursodeoxycholic acid conjugate (49) was the most potent, with IC50 values

  合成了一系列双氢青蒿素衍生物，并评估了它们对癌细胞的抗增殖活性。结构-活性关系研究发现了具有广谱抗增殖活性的二氢青蒿素-胆汁酸缀合物。其中，二氢青蒿素-熊去氧胆酸缀合物(49)是最有效的，在测试其对 15 种不同癌细胞系的抑制特性时，IC 50值在 0.04 至 0.96 μM 之间。体内实验表明，化合物49在A549细胞异种移植模型中以10mg/kg体重的剂量和在Lewis肺癌细胞移植模型中以12mg/kg体重的剂量有效抑制肿瘤生长。