(2S)-3-azido-2-hydroxypropyl p-toluenesulfonate | 136459-47-7

• 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: (2S)-3-azido-2-hydroxypropyl p-toluenesulfonate
• 英文别名: [(2S)-3-azido-2-hydroxypropyl] 4-methylbenzenesulfonate
• CAS: 136459-47-7
• 化学式: C₁₀H₁₃N₃O₄S
• 分子量: 271.297
• InChiKey: GSOZMIFQWCNBHZ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-3-azido-2-hydroxypropyl p-toluenesulfonate 、 2-(1-methylethoxy)phenyl-1-piperazine 在 三乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 30.0h， 以66%的产率得到(R)-α-(azidomethyl)-4-[2-(1-methylethoxy)phenyl]-1-piperazineethanol
  参考文献：
  名称：

  Design, synthesis and biological evaluation of pyridine-phenylpiperazines: A novel series of potent and selective α1a-adrenergic receptor antagonist

  摘要：

  Beginning from the screening hit and literature alpha(1)-adrenergic compounds, a hybridized basic skeleton A was proposed as the pharmacophore for potent and selective alpha(1a)-AR antagonists. Introduction of a hydroxy group to increase the flexibility afforded B which served as the screening model and resulted in the identification of the second-generation lead 1. Using the Topliss approach, a number of potent and selective alpha(1a)-AR antagonists were discovered. In all cases, binding affinity and selectivity at the alpha(1a)-AR of S-hydroxy enantiomers were higher than the R-hydroxy enantiomers. As compared to the des-hydroxy analogues, the S-hydroxy enantiomers displayed comparable potency and better selectivity at alpha(1a)-AR. The S-hydroxy enantiomer 17 (K-i = 0.79 nM; alpha(1b)/alpha(1a) = 800; alpha(1d)/alpha(1a) = 104) was slightly less potent but much more selective at alpha(1a)-AR than tamsulosin (K-i = 0.13 nM, alpha(1b)/alpha(1a) = 15, alpha(1d)/alpha(1a) = 1.4). Compound 17 displayed higher selectivity in inhibiting rat prostate contraction over rat aorta contraction and also exhibited a higher degree of uroselectivity than tamsulosin in the anesthetized dog model. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00151-6
• 作为产物：
  描述：

  (S)-1-azido-2-trimethylsilyloxy-3-tosyloxypropane 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (2S)-3-azido-2-hydroxypropyl p-toluenesulfonate
  参考文献：
  名称：

  由钛（O-介导的硅烷缩水甘油基衍生物的开环我-1- PR）4或Al（O-我-Pr）3：访问多功能Ç 3积木。

  摘要：

  Ti（O- i- Pr）4或Al（O- i- Pr）3催化的Me 3 SiN 3或Me 3 SiCN催化手性缩水甘油或甲苯磺酸缩水甘油酯的开环反应是区域特异性的，并且立体选择性很高，导致新的三功能手性构建基块。通过Mosher酯衍生物的1 H NMR测定，开环产物的对映体过量为90-95％，这表明在开环过程中光学纯度没有明显降低。该方法用于在94％ee（丙醇类似物的前体）中一锅合成（R）-1-叠氮基-3-萘氧基-2-羟基丙烷。

  DOI：

  10.1016/s0957-4166(00)82168-0

文献信息

• Synthesis of Base-Modified "Abbreviated" NAD Analogues
  作者：Kristina Juricová、Svatava Smrčková、Antonín Holý

  DOI：10.1135/cccc19950237

  日期：——

  The "abbreviated" model of NAD, 1-[3-(adenin-9-yl)-2-hydroxypropyl]-3-carbamoylpyridinium chloride (VIIIa), and its 2,6-diaminopurine (VIIIb), 3-deazaadenine (VIIIc), guanine (VIIId) and cytosine (VIIIe) analogues were prepared by the Zincke reaction. The (R)-isomer of the adenine model VIIIa (compound IX) was prepared for chiroptical studies. As shown by NMR, UV and CD spectra, neither in dimethyl sulfoxide nor in water any intramolecular π-π interactions exist between the heteroaromatic systems.

  NAD的"缩写"模型，1-[3-(腺嘌呤-9-基)-2-羟基丙基]-3-氨基吡啶盐酸盐（VIIIa），以及其2,6-二氨基嘌呤（VIIIb），3-去氧腺嘌呤（VIIIc），鸟嘌呤（VIIId）和胞嘧啶（VIIIe）类似物通过Zincke反应制备。腺嘌呤模型VIIIa的（R）-异构体（化合物IX）已为手性光学研究做好准备。根据NMR、UV和CD光谱显示，无论在二甲基亚砜还是水中，异芳香系统之间不存在任何分子内π-π相互作用。
• Phthalimido arylpiperazines useful in the treatment of benign prostatic hyperplasia
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：US06362338B1

  公开（公告）日：2002-03-26

  This invention relates to a series of substituted piperazines of Formula II, as well as enantiomers thereof These compounds are useful in the manufacture of pharmaceutical compositions.

  这项发明涉及到一系列Formula II的替代哌嗪，以及其对映体。这些化合物在制药组合物的制造中是有用的。
• [EN] PHTALIMIDO ARYLPIPERAZINES AS ALPHA 1A RECEPTOR ANTAGONISTS USEFUL IN THE TREATMENT OF BENIGN PROSTATIC HYPERPLASIA<br/>[FR] PHTALIMIDO-ARYLPIPERAZINES UTILES DANS LE TRAITEMENT DE L'HYPERPLASIE PROSTATIQUE BENIGNE EN TANT QU'ANTAGONISTES DU RECEPTEUR ALPHA IA
  申请人：ORTHO-McNEIL PHARMACEUTICAL, INC.

  公开号：WO1999042445A1

  公开（公告）日：1999-08-26

  (EN) This invention relates to a series of heterocyclic substituted piperazines of Formula (I), pharmaceutical compositions containing them and intermediates used in their manufacture. The compounds of the invention selectively inhibit binding to the $g(a)-1a adrenergic receptor, a receptor which has been implicated in benign prostatic hyperplasia. As such the compounds are potentially useful in the treatment of this disease.(FR) L'invention concerne une série de pipérazines hétérocycliques substituées représentées par la formule I: (I), ainsi que des compositions pharmaceutiques contenant ces pipérazines et des intermédiaires utilisé dans la préparation de ces dernières. Ces composés inhibent de manière sélective la liaison au récepteur adrénergique $g(a)-1a, un récepteur dont on a démontré le rôle dans l'hyperplasie prostatique bénigne. Ces composés présentent par conséquent une utilité potentielle pour le traitement de cette pathologie.

  该发明涉及一系列Formula (I)的杂环取代哌嗪、包含它们的制药组合物和用于其制造的中间体。该发明的化合物选择性地抑制与$g(a)-1a肾上腺素能受体的结合，该受体已被证明在良性前列腺增生中起作用。因此，这些化合物在治疗该疾病方面具有潜在的用途。
• Copper-Catalyzed Asymmetric Sulfonylative Desymmetrization of Glycerol
  作者：Kosuke Yamamoto、Keisuke Miyamoto、Mizuki Ueno、Yuki Takemoto、Masami Kuriyama、Osamu Onomura

  DOI：10.3390/molecules27249025

  日期：——

  Glycerol is the main side product in the biodiesel manufacturing process, and the development of glycerol valorization methods would indirectly contribute the sustainable biodiesel production and decarbonization. Transformation of glycerol to optically active C3 units would be one of the attractive routes for glycerol valorization. We herein present the asymmetric sulfonylative desymmetrization of glycerol by using a CuCN/(R,R)-PhBOX catalyst system to provide an optically active monosulfonylated glycerol in high efficiency. A high degree of enantioselectivity was achieved with a commercially available chiral ligand and an inexpensive carbonate base. The optically active monosulfonylated glycerol was successfully transformed into a C3 unit attached with differentially protected three hydroxy moieties. In addition, the synthetic utility of the present reaction was also demonstrated by the transformation of the monosulfonylated glycerol into an optically active synthetic ceramide, sphingolipid E.

  甘油是生物柴油制造过程中的主要副产品，发展甘油利用方法将间接促进可持续生物柴油生产和减碳。将甘油转化为光学活性的C3单元将是甘油价值化的一种有吸引力的途径。本文介绍了使用CuCN/(R,R)-PhBOX催化剂体系对甘油进行不对称磺酰化去对称化反应，以高效率提供光学活性单磺酰化甘油。使用商业可得的手性配体和廉价碳酸盐碱基实现了高度对映选择性。成功将光学活性单磺酰化甘油转化为连接有三个不同保护的羟基官能团的C3单元。此外，本反应的合成效用也通过将单磺酰化甘油转化为光学活性合成鞘脂类E证明了。
• Phthalimido arylpiperazines as alpha 1A receptor antagonists useful in the treatment of benign prostatic hyperplasia
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP1346983A2

  公开（公告）日：2003-09-24

  This invention relates to a series of heterocyclic substituted piperazines of Formula (I), pharmaceutical compositions containing them and intermediates used in their manufacture. The compounds of the invention selectively inhibit binding to the α-1a adrenergic receptor, a receptor which has been implicated in benign prostatic hyperplasia. As such the compounds are potentially useful in the treatment of this disease.

  本发明涉及一系列式（I）的杂环取代哌嗪类化合物、含有这些化合物的药物组合物以及用于制造这些化合物的中间体。本发明的化合物可选择性地抑制与 α-1a 肾上腺素能受体的结合，该受体与良性前列腺增生症有关。因此，本发明化合物可用于治疗这种疾病。