四氢-4-(5-羟戊基)-(3AS,4S,6AR)-1H-噻吩并[3,4-D]咪唑-2(3H)-酮 | 53906-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并咪唑类化合物
• 中文名称: 四氢-4-(5-羟戊基)-(3AS,4S,6AR)-1H-噻吩并[3,4-D]咪唑-2(3H)-酮
• 英文名称: biotinol
• 英文别名: (3aS,4S,6aR)-4-(5-hydroxy-pentyl)tetrahydrothieno[3,4-d]imidazol-2-one；(3aS,4S,6aR)-4-(5-hydroxypentyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one；(3aS,4S,6aR)-4-(5-hydroxypentyl)-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-2-one
• CAS: 53906-36-8
• 化学式: C₁₀H₁₈N₂O₂S
• 分子量: 230.331
• InChiKey: RGIKRHKHRAAZIO-CIUDSAMLSA-N

物化性质

• 沸点：
  500.0±35.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)
• 溶解度：
  甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  86.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  D-生物素	biotin	58-85-5	C10H16N2O3S	244.315
  D-生物素甲酯	biotin methyl ester	608-16-2	C11H18N2O3S	258.342
  (1E)-1-(4-氯苯基)-2,2,2-三氟乙酮O-(1,3-二噁戊环-2-基甲基)肟	(+)-biotin ethyl ester	87573-52-2	C12H20N2O3S	272.368
  (+)生物素-N-琥珀酰亚胺基酯	biotin N-Hydroxysuccinimide ester	35013-72-0	C14H19N3O5S	341.388
  五氟苯酚生物素酯	biotin pentafluorophenyl ester	120550-35-8	C16H15F5N2O3S	410.365
  1’N-苄基生物素	5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid	76335-62-1	C17H22N2O3S	334.439

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(+)-deoxybiotin	——	C10H18N2OS	214.332
  ——	biotinamine	135242-89-6	C10H19N3OS	229.346
  ——	(3aS,4S,6aR)-4-hept-6-ynyl-tetrahydro-thieno[3,4-d]imidazol-2-one	887915-53-9	C12H18N2OS	238.354
  ——	(3aS,4S,6aR)-4-(5-bromo-pentyl)tetrahydrothieno[3,4-d]imidazol-2-one	304439-23-4	C10H17BrN2OS	293.228
  ——	biotin-aldehyde	——	C10H16N2O2S	228.315
  ——	1H-thieno<3,4-d>imidazol-2(3H)-one, tetrahydro-4-(5-chloropentyl)-, <3aS-(3aα,4β,6aα)>-	——	C10H17ClN2OS	248.777
  生物素-C5-叠氮	(3aS,4S,6aR)-4-(5-azido-pent-1-yl)tetrahydrothieno[3,4-d]imidazol-2-one	1260586-88-6	C10H17N5OS	255.344
  ——	5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentyl dimethyl phosphite	1231709-98-0	C12H23N2O4PS	322.365
  ——	biotin methanesulfonate	146395-18-8	C11H20N2O4S2	308.423
  ——	5-((3aR,6S,6aS)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-6-yl)pentyl 2,2-diphenylacetate	1265716-37-7	C24H28N2O3S	424.564

反应信息

• 作为反应物：
  描述：

  四氢-4-(5-羟戊基)-(3AS,4S,6AR)-1H-噻吩并[3,4-D]咪唑-2(3H)-酮 在 吡啶 、 盐酸 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (3aS,3a'S,4S,4'S,6aR,6a'R)-4,4'-(((((5-(1-(3-(((Z)-4-amino-2-fluorobut-2-en-1-yl)sulfonyl)benzyl)-1H-1,2,3-triazol-4-yl)-1,3-phenylene)bis(oxy))bis(propane-3,1-diyl))bis(1H-1,2,3-triazole-4,1-diyl))bis(pentane-5,1-diyl))bis(tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one) hydrochloride
  参考文献：
  名称：

  [EN] BIOPROBES FOR LYSYL OXIDASES AND USES THEREOF
  [FR] BIOSONDES POUR LYSYL OXYDASES ET LEURS UTILISATIONS

  摘要：

  本发明涉及能够结合特定胺氧化酶的新型生物探针。这些生物探针在检测和确定样本中特定胺氧化酶的浓度的方法中是有用的，同时也可用于定量评估特定胺氧化酶的抑制方法。

  公开号：

  WO2021155439A1
• 作为产物：
  描述：

  (+)生物素-N-琥珀酰亚胺基酯 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 4.0h， 以67%的产率得到四氢-4-(5-羟戊基)-(3AS,4S,6AR)-1H-噻吩并[3,4-D]咪唑-2(3H)-酮
  参考文献：
  名称：

  Evaluation of a vitamin-cloaking strategy for oligopeptide therapeutics: biotinylated HIV-1 protease inhibitors

  摘要：

  The outstanding limitations to the oligopeptide as a therapeutic agent are poor oral availability and rapid biliary clearance. To address these concerns a series of eight peptidic HIV-1 protease inhibitors containing the structural segment of the vitamin biotin have been prepared. These have been evaluated with regard to the hypothesis that this vitamin would cloak the peptidic character of these oligopeptides, and thus impart to these inhibitors the potential for absorption and distribution via biotin transporters and receptors. By iterative optimization about a -Chal psi[CH- (OH)CH(OH)]Val- core inhibitory insert, three particularly potent inhibitors (K-i less than or equal to 10 nM) of the HIV-1 protease were obtained. Although excellent cell culture antiviral activity is observed for other peptidic protease inhibitors of comparable affinity, none in this series exhibited satisfactory antiviral activity. This failure is-attributed to the incompatibility of the hydrophilic and hydrogen-bonding biotin segment, with the facile membrane permeability and intracellular access presumably required for antiviral activity. The ability of the biotin to cloak the peptide, and thus render the overall appearance of the conjugate as that of a vitamin, was evaluated. Four of this series were evaluated for recognition by the Caco-2 cell intestinal biotin transporter, None inhibited competitively biotin uptake, indicating a lack of recognition. A vitamin may bind to a specific protein carrier, and thus attain an improved serum profile (by resistance to biliary clearance) and advantageous delivery to cells. Therefore, the serum concentrations of three were evaluated following an iv bolus in a rat model for serum clearance. One of the three protease inhibitors (L-idonamide, 6-cyclohexyl-2,5,6-trideoxy-2-(1-methylethyl)-5-[[3-methyl-1-oxo-2-[[5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)-1-oxopentyl]amino]butyl]amino]-N-[2-methyl-1-[[(2-pyridinylmethyl)amino] carbonyl]butyl]-, [3aS-[3a alpha,4 beta(1R*,2R*;3R*),6a alpha]]-) sustained a more than 5-fold increase in serum concentration at all time points relative to the benchmark structure. The remaining two had serum concentrations at least equal to the benchmark, suggestive of improved resistance to clearance. One(L-idonamide, 6-cyclohexyl-2,5,6-trideoxy-5-[[2-[[5-(hexahydro-2-oxo-1H-thieno-[3,4-d]imidazol-4-yl)pentyl]thio]benzoyl]amino]-2-(1-methylethyl)-N-[2-methyl-1-[[(2-pyridinyl- methyl)amino]carbonyl]butyl]-, [3aS-[3a alpha,4 beta(1R*,2R*),6a alpha]]-) was prepared as a complex with the biotin-binding protein avidin. Avidin may resemble an endogenous serum biotin carrier protein. The antiviral activity (evaluated in an H9-HTLV(IIIB) acute HIV-1 infection assay) of the inhibitor and the avidin complex was identical. This suggests that the avidin-inhibitor complex is capable of cell internalization. Although the weak antiviral activity of these biotinylated inhibitors precludes consideration as practical HIV therapeutics, the overall data remain suggestive of vitamin cloaking of oligopeptides as a strategy of potential value.

  DOI：

  10.1021/jm00028a013

文献信息

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  DOI：10.1021/jacs.6b02344

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  DOI：10.1021/jacs.1c06014

  日期：2021.9.15

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• 2-Azaadamantane<i>N</i>-oxyl (AZADO)/Cu Catalysis Enables Chemoselective Aerobic Oxidation of Alcohols Containing Electron-Rich Divalent Sulfur Functionalities
  作者：Yusuke Sasano、Naoki Kogure、Shota Nagasawa、Koki Kasabata、Yoshiharu Iwabuchi

  DOI：10.1021/acs.orglett.8b02528

  日期：2018.10.5

  The chemoselective oxidation of alcohols containing electron-rich sulfur functionalities (e.g., 1,3-dithianes and sulfides) into their corresponding carbonyl compounds with the sulfur groups can sometimes be a demanding task in modern organic chemistry. A reliable method for this transformation, which features azaadamantane-type nitroxyl radical/copper catalysis using ambient air as the terminal oxidant

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• AVOIDANCE OF NON-SPECIFIC BINDING ON AN ACOUSTIC WAVE BIOSENSOR USING LINKER AND DILUENT MOLECULES FOR DEVICE SURFACE MODIFICATION
  申请人：THOMPSON Michael

  公开号：US20110306771A1

  公开（公告）日：2011-12-15

  An acoustic wave biosensor comprising a surface of a mixed self-assembling monolayer for receiving a probe-biomolecule is described herein. The biosensor surface may comprise a piezoelectric quartz crystal,—for detection purposes with the electromagnetic piezoelectric acoustic sensor (EMPAS)—upon which a mixed self-assembling monolayer is formed, which includes at least one linker, such as 2,2,2-trifluoroethyl-13-trichlorosilyl-tridecanoate (TTTA); its oligoethylene glycol (OEG) analog OEGylated TTTA (OEG-TTTA); S-(2-(2-(2-(3-trichlorosilyl-propyloxy)-ethoxy)-ethoxy)-ethyl)-benzenethiosulfonate (OEG-TU BTS). Linker/diluent systems for attaching a functionalizing entity to the surface of a biosensor are described, as well as methods for preparing a biosensor surface with an oligoethylene glycol linker.

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• [EN] SYNTHETIC RECEPTORS FOR IONOPHORIC COMPOUNDS<br/>[FR] RÉCEPTEURS SYNTHÉTIQUES POUR COMPOSÉS IONOPHORES
  申请人：UNIV GENT

  公开号：WO2019166475A1

  公开（公告）日：2019-09-06

  The present invention relates to synthetic receptors for ionophoric compounds, such as ionophoric toxins. Hence, the invention provides synthetic molecules capable of binding different ionophoric compounds, thereby being suitable for use in the detection, isolation and detoxification of such ionophoric compounds. The present invention further provides the use of such synthetic receptors in human and veterinary medicine, such as in the diagnosis, prevention and/or treatment of disorders caused by such ionophoric compounds. Finally, the invention provides methods of preparing such synthetic receptors for ionophoric compounds.

  本发明涉及用于离子载体化合物的合成受体，例如离子载体毒素。因此，本发明提供了能够结合不同离子载体化合物的合成分子，从而适用于检测、分离和解毒此类离子载体化合物。本发明还提供了在人类和兽医学中使用这种合成受体的方法，例如在诊断、预防和/或治疗由这类离子载体化合物引起的疾病。最后，本发明提供了制备此类离子载体化合物的合成受体的方法。