methyl 2-(5-(benzo[d][1,3]dioxol-5-yl)-2H-tetrazol-2-yl)acetate | 1605294-08-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(5-(benzo[d][1,3]dioxol-5-yl)-2H-tetrazol-2-yl)acetate
• 英文别名: Methyl 2-(5-(benzo[d][1,3]dioxol-5-yl)-2H-tetrazol-2-yl)acetate；methyl 2-[5-(1,3-benzodioxol-5-yl)tetrazol-2-yl]acetate
• CAS: 1605294-08-3
• 化学式: C₁₁H₁₀N₄O₄
• 分子量: 262.225
• InChiKey: KAVNXQIYACNBDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  88.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-(5-(benzo[d][1,3]dioxol-5-yl)-2H-tetrazol-2-yl)acetate 在 4-二甲氨基吡啶 、 草酰氯 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 (R)-2-(2-(5-(benzo[d][1,3]dioxol-5-yl)-2H-tetrazol-2-yl)-N-cyclohexylacetamido)-N-cyclopentylpropanamide
  参考文献：
  名称：

  [EN] HETEROCYCLE-BISAMIDE INHIBITORS OF SCAVENGER RECEPTOR BI
  [FR] INHIBITEURS HÉTÉROCYCLE - BISAMIDE DE RÉCEPTEUR ÉBOUEUR BI

  摘要：

  公开号：

  WO2014063168A8
• 作为产物：
  描述：

  胡椒腈 在 sodium azide 、 potassium carbonate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 42.5h， 生成 methyl 2-(5-(benzo[d][1,3]dioxol-5-yl)-2H-tetrazol-2-yl)acetate
  参考文献：
  名称：

  [EN] HETEROCYCLE-BISAMIDE INHIBITORS OF SCAVENGER RECEPTOR BI
  [FR] INHIBITEURS HÉTÉROCYCLE - BISAMIDE DE RÉCEPTEUR ÉBOUEUR BI

  摘要：

  公开号：

  WO2014063168A8

文献信息

• HETEROCYCLE-BISAMIDE INHIBITORS OF SCAVENGER RECEPTOR BI
  申请人：THE BROAD INSTITUTE, INC.

  公开号：US20150284371A1

  公开（公告）日：2015-10-08

  This application describes compounds and methods that can inhibit Scavenger receptor class B, type I (SR-BI) activity, which compounds and methods can be used, for example, to mediate high-density lipoprotein (HDL) lipid uptake and treat hepatitis C viral infections. The compounds have the formula: wherein R 1 and R 2 are independently H, halogen, cyano, haloalkyl, haloalkyloxy or OMe; or R 1 and R 2 together are —O—CH 2 — or -0- CF 2 —O—; R 3 is H, halogen, cyano, haloalkyl or haloalkyloxy; R 4 is C 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkylmethyl or C 3-6 cycloheteroalkyl, wherein the heteroatom is N or 0; R 5 is H or CH 3 ; R 6 is C 1-6 alkyl or C 3-6 cycloalkyl; and A, B, D and E are each, independently, CH, N, 0 or S, wherein at least one of A, B, D and E is N, and another of A, B, D and E is N, 0 or S.

  该申请描述了一种可以抑制清道夫受体B类，类型I（SR-BI）活性的化合物和方法，这些化合物和方法可以用于介导高密度脂蛋白（HDL）脂质摄取和治疗丙型肝炎病毒感染。这些化合物的化学式为：其中R1和R2独立地为H，卤素，氰基，卤代烷基，卤代烷氧基或OMe；或者R1和R2在一起为—O—CH2—或-0-CF2—O—；R3为H，卤素，氰基，卤代烷基或卤代烷氧基；R4为C1-6烷基，C3-6环烷基，C3-6环烷基甲基或C3-6环杂烷基，其中杂原子为N或O；R5为H或CH3；R6为C1-6烷基或C3-6环烷基；而A、B、D和E分别独立地为CH、N、O或S，其中至少一个为N，另一个为N、O或S。
• Discovery of bisamide-heterocycles as inhibitors of scavenger receptor BI (SR-BI)-mediated lipid uptake
  作者：Chris Dockendorff、Patrick W. Faloon、Andrew Germain、Miao Yu、Willmen Youngsaye、Partha P. Nag、Melissa Bennion、Marsha Penman、Thomas J.F. Nieland、Sivaraman Dandapani、José R. Perez、Benito Munoz、Michelle A. Palmer、Stuart L. Schreiber、Monty Krieger

  DOI：10.1016/j.bmcl.2015.03.074

  日期：2015.6

  A new series of potent inhibitors of cellular lipid uptake from HDL particles mediated by scavenger receptor, class B, type I (SR-BI) was identified. The series was identified via a high-throughput screen of the National Institutes of Health Molecular Libraries Small Molecule Repository (NIH MLSMR) that measured the transfer of the fluorescent lipid DiI from HDL particles to CHO cells overexpressing SR-BI. The series is characterized by a linear peptidomimetic scaffold with two adjacent amide groups, as well as an aryl-substituted heterocycle. Analogs of the initial hit were rapidly prepared via Ugi 4-component reaction, and select enantiopure compounds were prepared via a stepwise sequence. Structure-activity relationship (SAR) studies suggest an oxygenated arene is preferred at the western end of the molecule, as well as highly lipophilic substituents on the central and eastern nitrogens. Compound 5e, with (R)-stereo-chemistry at the central carbon, was designated as probe ML279. Mechanistic studies indicate that ML279 stabilizes the interaction of HDL particles with SR-BI, and its effect is reversible. It shows good potency (IC50 = 17 nM), is non-toxic, plasma stable, and has improved solubility over our alternative probe ML278. (C) 2015 The Authors. Published by Elsevier Ltd.
• US9884851B2
  申请人：——

  公开号：US9884851B2

  公开（公告）日：2018-02-06
• [EN] HETEROCYCLE-BISAMIDE INHIBITORS OF SCAVENGER RECEPTOR BL<br/>[FR] INHIBITEURS HÉTÉROCYCLE - BISAMIDE DE RÉCEPTEUR ÉBOUEUR BL
  申请人：BROAD INST INC

  公开号：WO2014063168A1

  公开（公告）日：2014-04-24

  This appl ication describes compounds and methods that can inhibit Scavenger receptor class B, type I (SR-BI) activity, wh ich compounds and methods can be used, for example, to med iate h igh-density l ipoprotein (H DL) l ipid uptake and treat hepatitis C vira l infections. The compounds have the formu la : wherein R1 and R2 are independently H, halogen, cyano, haloalkyl, ha loa lkyloxy or OMe; or R1 and R2 together are -O-CH2-O- or -0- CF2-O-; R3 is H, ha logen, cyano, ha loalkyl or ha loa lkyloxy; R4 is C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkylmethyl or C3-6cycloheteroalkyl, wherein the heteroatom is N or 0; R5 is H or CH3; R6 is C1-6alkyl or C3-6cycloalkyl; and A, B, D and E are each, independently, CH, N, 0 or S, wherein at least one of A, B, D and E is N, and another of A, B, D and E is N, 0 or S.
• [EN] HETEROCYCLE-BISAMIDE INHIBITORS OF SCAVENGER RECEPTOR BI<br/>[FR] INHIBITEURS HÉTÉROCYCLE - BISAMIDE DE RÉCEPTEUR ÉBOUEUR BI
  申请人：BROAD INST INC

  公开号：WO2014063168A8

  公开（公告）日：2015-05-07