1,3-bis(4-methylphenoxy)propan-2-ol | 14569-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-bis(4-methylphenoxy)propan-2-ol
• 英文别名: 1,3-di(p-tolyloxy)-2-propanol；1,3-bis-p-tolyloxy-propan-2-ol；2-Hydroxy-1.3-di-p-tolyloxy-propan；1.3-Di-p-tolyloxy-propanol-(2)；β.β'-Di-p-kresoxy-isopropylalkohol；β-Oxy-α.γ-di-p-kresoxy-propan
• CAS: 14569-62-1
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: GUKUMDDKDYSDBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bis(4-methylphenoxy)propan-2-ol 在 吡啶 、 氯仿 、 三氯氧磷 作用下， 生成 glyceryl phosphate
  参考文献：
  名称：

  Boyd; Ladhams, Journal of the Chemical Society, 1928, p. 221

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲酚 在 1,4-二氧六环 、 sodium hydroxide 作用下， 生成 1,3-bis(4-methylphenoxy)propan-2-ol
  参考文献：
  名称：

  Glycerol Ethers. I. Alkaminoalkyl Ethers of 1,3-Bis-(aryloxy)-2-propanols and Related Compounds

  摘要：

  DOI：

  10.1021/ja01640a039

文献信息

• Hypocholesterolemic activity of 1,3-bis(substituted phenoxy)-2-propanones
  作者：Claude Piantadosi、Iris H. Hall、Steven D. Wyrick、Khalid S. Ishaq

  DOI：10.1021/jm00224a006

  日期：1976.2

  phenoxy)-2-propanones was found to be active hypocholesterolemic agents at 10 mg/kg/day. The p-chloro- and p-methyl-substituted phenoxy compounds possess the highest activity. These compounds did not possess the estrogenic and antifertility activities of the related previously reported derivatives of the bis(beta-phenylethyl) ketone series. The 1,3-bis(p-methylphenoxy)-2-propanone (7) also lowered serum triglycerides

  发现一系列的1,3-双（取代的苯氧基）-2-丙烷是有效的降胆固醇药，剂量为10 mg / kg / day。对氯-和对甲基取代的苯氧基化合物具有最高的活性。这些化合物不具有以前报道过的双（β-苯乙基）酮系列相关衍生物的雌激素和抗生育活性。1,3-双（对甲基苯氧基）-2-丙酮（7）也会降低血清甘油三酸酯和甘油，这似乎是由于血清脂肪酶水平升高和肝脂肪酶活性降低所致。肝脏减少了游离脂肪酸向复杂脂质中的掺入。胆固醇在治疗的动物中排泄更快。
• Synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines
  作者：Stefânia N. Lavorato、Mariana C. Duarte、Daniela P. Lage、Carlos A. P. Tavares、Eduardo A. F. Coelho、Ricardo J. Alves

  DOI：10.1007/s00044-017-1805-1

  日期：2017.5

  We describe herein the antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines, prepared in four simple steps from epichlorohydrin. Among the evaluated compounds, three (4o, 4q, and 4r) displayed considerable activity against Leishmania amazonensis promastigote forms, with IC50 values below 10 µM. We also analyzed the effects of the nature and the position of ring substituent on activity. Two amines

  我们在这里描述了从表氯醇四个简单步骤制备的1,3-双（芳氧基）丙-2-胺的抗衰老活性。在所评估的化合物中，三个（4o，4q和4r）显示出对亚马逊利什曼原虫前鞭毛体形式的相当大的活​​性，IC 50值低于10 µM。我们还分析了环取代基的性质和位置对活性的影响。两种胺（4m和4o）在处理被亚马逊菌感染的巨噬细胞时表现出出色的特性，在测试浓度下将寄生虫负担降低了95％以上。
• The Hormonal Milieu in Early Stages of Bone Cell Differentiation Modifies the Subsequent Sex-Specific Responsiveness of the Developing Bone to Gonadal Steroids
  作者：E. Berger、I. Bleiberg、Y. Weisman、B. Lifschitz-Mercer、L. Leider-Trejo、A. Harel、A. M. Kaye、D. Somjen

  DOI：10.1359/jbmr.2001.16.5.823

  日期：——

  We have established previously that rat bone tissue, as well as rat and human‐derived bone cells in culture, show a sex‐specific response to gonadal steroids in stimulation of the specific activity of the BB isozyme of creatine kinase (CK) and DNA synthesis. This response could be modified by manipulation of the endocrine environment during early stages in rat development. To further examine the influence of changing hormonal steroid milieu and vitamin D status on the action of gonadal steroids in developing bone tissue, we used two models of ectopic bone formation: demineralized tooth matrix (DTM) implanted under the skin, and femoral bone marrow (BM) transplanted under the kidney capsule of a syngeneic recipient mouse. The response to gonadal steroids in ossicles developed from implanted DTM depended on the recipient's gender; injection of estradiol 17β (E2; 5 μg) into young female mice 21 days after DTM implantation increased, 24 h later, CK activity in the newly formed ossicles by ∼60%, whereas injection of dihydrotestosterone (DHT; 50 μg) had no effect on CK activity. In contrast, in male mice, DHT but not E2 increased CK activity in the ossicles by ∼50%. This sex‐specific response was abolished in gonadectomized mice resulting in a similar response of the ossicles to both E2 and DHT. When DTM was implanted into vitamin D‐deficient female mice, there was a lower basal CK activity and a significantly diminished response to E2 in the newly formed bone tissues. When BM, which contains mesenchymal and stromal cells and committed osteoprogenitor cells, was transplanted into 6‐week‐old intact or gonadectomized female or male mice, the response of the newly formed bone ossicles, 21 days after transplantation, to E2 or to DHT was according to the gender of the donor. Bone formed from BM obtained from female mice responded to E2 only and those formed from male BM responded to DHT only. Ossicles developed from BM obtained from gonadectomized mice showed lack of response to either gonadal steroid. Furthermore, only ∼25% of the BM transplants obtained from castrated (CAST) male donors developed into ossicles. Ossicles formed from BM obtained from vitamin D‐deficient female donors showed lack of response to gonadal steroids. These findings suggest that the manipulation of the hormonal milieu in early stages of the differentiation sequence of bone cells modifies the subsequent selective responsiveness of the developing bone tissue to gonadal steroids.

  我们之前已经证实，大鼠骨组织以及培养中的大鼠和人类骨细胞对性腺类固醇有性别特异性反应，即刺激肌酸激酶（CK）BB 同工酶的特异性活性和 DNA 合成。在大鼠发育的早期阶段，这种反应可能会因内分泌环境的变化而改变。为了进一步研究激素类固醇环境和维生素 D 状态的变化对性腺类固醇作用于发育中骨组织的影响，我们使用了两种异位骨形成模型：植入皮下的去矿物质牙基质（DTM）和移植到合成受体小鼠肾囊下的股骨髓（BM）。植入 DTM 后 21 天，向幼年雌性小鼠注射雌二醇 17β（E2；5 μg），24 小时后，新形成的骨小泡中的 CK 活性增加了 60%，而注射双氢睾酮（DHT；50 μg）对 CK 活性没有影响。相反，在雄性小鼠中，DHT 而不是 E2 会使骨小梁中的 CK 活性增加 50%。在性腺切除的小鼠中，这种性别特异性反应被取消，导致听骨对 E2 和 DHT 的反应相似。当将 DTM 植入维生素 D 缺乏的雌性小鼠体内时，新形成的骨组织中的基础 CK 活性较低，对 E2 的反应也明显减弱。当将含有间充质细胞、基质细胞和坚定的成骨细胞的 BM 移植到 6 周大的完整或性腺切除的雌性或雄性小鼠体内时，移植 21 天后新形成的骨小梁对 E2 或 DHT 的反应与供体的性别有关。由雌性小鼠的骨髓形成的骨只对E2有反应，而由雄性小鼠的骨髓形成的骨只对DHT有反应。由性腺切除小鼠的骨髓形成的骨小梁对任何一种性腺类固醇都没有反应。此外，从阉割（CAST）雄性供体获得的骨髓移植只有 25% 发育成骨小泡。从维生素 D 缺乏的女性供体获得的骨髓形成的骨小体对性腺类固醇缺乏反应。这些研究结果表明，在骨细胞分化序列的早期阶段对激素环境的操纵会改变发育中的骨组织随后对性腺类固醇的选择性反应。
• 1,3-Bis(aryloxy)propan-2-ols as potential antileishmanial agents
  作者：Stefânia N. Lavorato、Mariana C. Duarte、Daniela P. Lage、Carlos A. P. Tavares、Eduardo A. F. Coelho、Ricardo J. Alves

  DOI：10.1111/cbdd.13024

  日期：2017.11

  We describe herein the synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-ols. Five compounds (2, 3, 13, 17, and 18) exhibited an effective antileishmanial activity against stationary promastigote forms of Leishmania amazonensis (IC50 < 15.0 μm), and an influence of compound lipophilicity on activity was suggested. Most of the compounds were poorly selective, as they showed toxicity

  我们在本文中描述了1，3-双（芳氧基）丙-2-醇的合成和抗衰老活性。五个化合物（2、3、13、17和18）对亚马逊利什曼原虫的固定前鞭毛体形式（IC50 <15.0μm）表现出有效的抗前鞭毛虫活性，并提出了化合物亲脂性对活性的影响。大多数化合物的选择性较差，因为它们对鼠类巨噬细胞显示毒性，只有17和18具有良好的选择指数（SI≥10.0）。选择了另外五种活性化合物（2、3、13、17和18）来治疗被感染的巨噬细胞，所有这些化合物都能够减少80％以上的内在寄生虫以及数量的减少。在至少一种测试浓度下，被感染的巨噬细胞数量增加了70％以上。共，
• Lefebvre; Levas, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1946, vol. 222, p. 1439
  作者：Lefebvre、Levas

  DOI：——

  日期：——