2-(S)-hydroxy-3-(3-methoxymethylphenyl)propan-1-ol trityl ether | 253350-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(S)-hydroxy-3-(3-methoxymethylphenyl)propan-1-ol trityl ether
• 英文别名: (2S)-3-(3-methoxymethylphenyl)-1-triphenylmethoxypropan-2-ol；(2S)-1-[3-(methoxymethyl)phenyl]-3-trityloxypropan-2-ol
• CAS: 253350-30-0
• 化学式: C₃₀H₃₀O₃
• 分子量: 438.566
• InChiKey: XCDOCEAMZQXLHW-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2-(S)-hydroxy-3-(3-methoxymethylphenyl)propan-1-ol trityl ether 在 吡啶 、 咪唑 、 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 Schwartz's reagent 、 正丁基锂 、 草酰氯 、 偶氮二异丁腈 、 二叔丁基过氧化物 、 (HF)n*Py 、 水 、 叔丁基锂 、 三正丁基氢锡 、 对甲苯磺酸 、 溶剂黄146 、 二甲基亚砜 、 甲基磺酰氯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 正戊烷 为溶剂， 反应 12.83h， 生成 甲基4-({2-[(1R,2R,3S)-3-羟基-2-{(1E)-3-羟基-4-[3-(甲氧基甲基)苯基]-1-丁烯-1-基}-5-氧代环戊基]乙基}硫基)丁酸酯
  参考文献：
  名称：

  Design and synthesis of a selective EP4-receptor agonist. Part 3: 16-phenyl-5-thiaPGE1 and 9-β-halo derivatives with improved stability

  摘要：

  To identify a new selective EP4-agonist with improved chemical stability, further chemical modification of those reported previously was continued. We focused our attention on chemical modification of the alpha chain of 3,7-dithiaPGE(1), and selected 5-thiaPGE(1), as a new chemical lead, Introduction of an optimized omega to chain to the 5-thiaPG skeleton afforded in-methoxymethyl derivative 33a, which showed the most potent EP4-receptor agonist activity and good subtype-selectivity both in vitro and in vivo. 9beta-HaloPGF derivatives were also synthesized and biologically evaluated in an attempt to block self-degradation of the beta-hydroxyketone moiety. Among these series, 39a and 39b showed potent agonist activity and good subtype-selectivity. Structure-activity relationships (SARs) are also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00031-7
• 作为产物：
  描述：

  1-溴-3-(甲氧基甲基)苯 、 三苯甲基-(S)-缩水甘油醚 在 copper(l) iodide 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 以95.8 g的产率得到2-(S)-hydroxy-3-(3-methoxymethylphenyl)propan-1-ol trityl ether
  参考文献：
  名称：

  Design and synthesis of a selective EP4-receptor agonist. Part 3: 16-phenyl-5-thiaPGE1 and 9-β-halo derivatives with improved stability

  摘要：

  To identify a new selective EP4-agonist with improved chemical stability, further chemical modification of those reported previously was continued. We focused our attention on chemical modification of the alpha chain of 3,7-dithiaPGE(1), and selected 5-thiaPGE(1), as a new chemical lead, Introduction of an optimized omega to chain to the 5-thiaPG skeleton afforded in-methoxymethyl derivative 33a, which showed the most potent EP4-receptor agonist activity and good subtype-selectivity both in vitro and in vivo. 9beta-HaloPGF derivatives were also synthesized and biologically evaluated in an attempt to block self-degradation of the beta-hydroxyketone moiety. Among these series, 39a and 39b showed potent agonist activity and good subtype-selectivity. Structure-activity relationships (SARs) are also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00031-7

文献信息

• A 3.7-dithiaprostanoic acid derivative
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0985663A1

  公开（公告）日：2000-03-15

  A 3,7-dithiaprostanoic acid derivative of the formula (I) (wherein, R1 is OH, C1∼6 alkyloxy, NR6R7 (R6, R7 are H, C1∼6 alkyl.); R2 is H, OH; R3 is single bond, C1∼6 alkylene; R4 is (i) C1∼8 alkyl substituted by C1∼6 alkyloxy, halogen etc., (ii) phenyloxy, C3∼7 cycloalkyloxy, (iii) furyl, furyloxy, thienyl, thienyloxy, naphthyl, naphthyloxy, phthalanyl, phthalanyloxy, (iv) phenyl, phenyloxy, C3∼7 cycloalkyl, C3∼7 cycloalkyloxy substituted by C1∼6 alkyl etc., (v) furyl, furyloxy, thienyl, thienyloxy, naphthyl, naphthyloxy, phthalanyl, phthalanyloxy substituted by C1∼6 alkyl etc.; R5 is H, C1∼6 alkyl.) can bind PGE2 receptor (particularly, EP4 subtype receptor) strongly. So, they are useful for the prevention and/or treatment of immunological diseases (autoimmune diseases, rejection after organ transplantation etc.), asthma, abnormal bone formation, neuronal cell death, liver damage, nephritis, hypertension, myocardiac ischemia and sleeping disorder etc.

  一种 3,7-二硫代前列腺酸衍生物，其式为(I) (其中，R1 是 OH、C1∼6 烷氧基、NR6R7（R6、R7 是 H、C1∼6 烷基）；R2 是 H、OH；R3 是单键、C1∼6 亚烷基；R4 是 (i) 被 C1∼6 烷氧基、卤素等取代的 C1∼8 烷基、(iii) 呋喃基、呋喃氧基、噻吩基、噻吩氧基、萘基、萘氧基、酞酰基、酞氧基， (iv) 被 C1∼6 烷基等取代的苯基、苯基氧基、C3∼7 环烷基、C3∼7 环烷氧基(v) 呋喃基、呋喃氧基、噻吩基、噻吩氧基、萘基、萘氧基、被 C1∼6 烷基取代的酞酰基、酞氧基等；R5 为 H、C1∼6 烷基）能与 PGE2 受体（尤其是 EP4 亚型受体）强烈结合。因此，它们可用于预防和/或治疗免疫性疾病（自身免疫性疾病、器官移植后的排斥反应等）、哮喘、骨骼形成异常、神经细胞死亡、肝损伤、肾炎、高血压、心肌缺血和睡眠障碍等。
• 5-THIA-OMEGA-SUBSTITUTED PHENYL-PROSTAGLANDIN E DERIVATIVES, PROCESS FOR PRODUCING THE SAME AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1097922A1

  公开（公告）日：2001-05-09

  5-Thia-ω-substituted phenyl-prostaglandin E derivatives represented by general formula (I) wherein each symbol is as defined in the specification. Because of being capable of bonding strongly to PEG2receptors (in particular, the subtype EP4), the compounds represented by general formula (I) are expected as useful in preventing and/or treating immunologic diseases, asthma, bone dysplasia, nerve cell death, lung failure, hepatopathy, acute hepatitis, nephritis, renal insufficiency, hypertension, myocardial ischemia, systemic inflammatory syndrome, ambustion pain, sepsis, hemophagous syndrome, macrophage activation syndrome, Still disease, Kawasaki disease, burn, systemic granulomatosis, ulcerative colitis, Crohn's disease, hypercytokinemia at dialysis, multiple organ failure, shock, etc. Moreover, these compounds participate in sleep disorders and platelet aggregation and, therefore, are expected as useful in preventing/treating these diseases.

  通式（I）代表的 5-噻-ω-取代苯基-前列腺素 E 衍生物，其中各符号如说明书中所定义。肾功能不全、高血压、心肌缺血、全身炎症综合征、灸痛、败血症、嗜血综合征、巨噬细胞活化综合征、斯蒂尔病、川崎病、烧伤、全身肉芽肿病、溃疡性结肠炎、克罗恩病、透析时的高细胞血症、多器官衰竭、休克等。此外，这些化合物还参与睡眠障碍和血小板聚集，因此有望用于预防/治疗这些疾病。
• US6043275A
  申请人：——

  公开号：US6043275A

  公开（公告）日：2000-03-28
• US6462081B1
  申请人：——

  公开号：US6462081B1

  公开（公告）日：2002-10-08
• US6586468B1
  申请人：——

  公开号：US6586468B1

  公开（公告）日：2003-07-01