(R)-3-azido-2-methyl-1-propanol | 245125-87-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (R)-3-azido-2-methyl-1-propanol
• 英文别名: (2R)-3-Azido-2-methyl-1-propanol；(R)-(-)-3-azido-2-methylpropanol；(2R)-3-azido-2-methylpropan-1-ol
• CAS: 245125-87-5
• 化学式: C₄H₉N₃O
• 分子量: 115.135
• InChiKey: KHEWKGAWXVDIJJ-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-azido-2-methyl-1-propanol 在 jones reagent 作用下， 以 丙酮 为溶剂， 以100%的产率得到3-azido-(2R)-methylpropanoic acid
  参考文献：
  名称：

  Total Synthesis of Cryptophycins and Their 16-(3-Phenylacryloyl) Derivatives

  摘要：

  Cryptophycin A, a cyclic depsipeptide isolated from the blue-green alga (cyanobacterium) Nostoc sp.GSV 224, has shown excellent activity against solid tumors implanted in mice. The benzylic epoxide, which was shown to be very important for biological, activity, is also fairly unstable under both acidic and alkaline conditions. The high doses needed to observe in vivo activity might be a result of this instability. In order to solve this problem while preserving the electrophilic character of the benzylic position, enones 1 and 2 have been proposed as promising analogs of the natural product, and a convergent total synthesis of these compounds is described. In addition, the same strategy was used to prepare Cryptophycins A, B, C, and D.

  DOI：

  10.1021/jo960816b
• 作为产物：
  描述：

  (S)-(+)-3-溴-2-甲基-1-丙醇 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以82%的产率得到(R)-3-azido-2-methyl-1-propanol
  参考文献：
  名称：

  羟烷基叠氮化物与酮的不对称施密特反应

  摘要：

  Schmidt 反应的不对称等价物允许在对称环己酮的扩环中进行立体控制。该过程包括手性 1,2- 和 1,3- 羟烷基叠氮化物与酮在酸催化下的反应；初始反应提供亚胺醚，随后可以用碱打开。报道了对该反应的系统研究，其中酮底物、手性羟烷基叠氮化物和反应条件各不相同。选择性高达约。98:2 可用于合成取代的己内酰胺，整个过程中最多涉及 1,7-立体选择。任何一种可能的迁移碳在电子上是相同的，这一事实为研究完全由立体电子因素控制的扩环反应提供了一个不寻常的机会。

  DOI：

  10.1021/ja0348896

文献信息

• Novel carbapenem derivatives of quarternary salt type
  申请人：——

  公开号：US20030022881A1

  公开（公告）日：2003-01-30

  An objective of the present invention is to provide carbapenem derivatives which have potent antibiotic activity against MRSA, PRSP, Influenzavirus, and &bgr;-lactamase-producing bacteria and are stable against DHP-1. The compounds according to the present invention are compounds represented by formula (I) or pharmaceutically acceptable salts thereof: 1 wherein R 1 represents H or methyl; R 2 and R 3 each independently represent H, halogen, lower alkyl or the like; R 4 represents optionally substituted lower alkylthio or the like; and R 5 represents optionally substituted lower alkyl or the like.

  本发明的目的在于提供对MRSA、PRSP、流感病毒和β-内酰胺酶产生菌具有强大抗生素活性的碳青霉烯衍生物，且对DHP-1稳定。根据本发明的化合物是由公式(I)表示的化合物或其药物可接受的盐：1其中R1代表H或甲基；R2和R3各自独立地代表H、卤素、低级烷基等；R4代表可选地取代的低级烷基亚磺酰基等；R5代表可选地取代的低级烷基等。
• Carbapenem antibacterial compounds, compositions containing such
  申请人：Merck & Co., Inc.

  公开号：US06140318A1

  公开（公告）日：2000-10-31

  Compounds of formula I are disclosed. ##STR1## as well as pharmaceutically acceptable salts thereof. The naphthosultam is substituted with various substituent groups including at least one cationic group -A-Q-L-B. The carbapenems of the invention are effective against susceptible bacterial organisms, including methicillin resistant Staphylococcus aureus (MRSA), methicillin resistant Staphylococcus epidermidis (MRSE), and methicillin resistant coagulase negative Staphylococci (MRCNS).

  公式I的化合物已被披露。##STR1##以及其药用盐。萘磺胺酮被各种取代基替代，包括至少一个阳离子基团-A-Q-L-B。本发明的碳青霉烯对易感染的细菌有有效作用，包括耐甲氧西林金黄色葡萄球菌（MRSA）、耐甲氧西林表皮金黄色葡萄球菌（MRSE）和耐甲氧西林凝血酶阴性金黄色葡萄球菌（MRCNS）。
• Carbapenem antibacterial compounds, compositions containing such compounds and methods of treatment
  申请人：Merck & Co., Inc.

  公开号：US06294529B1

  公开（公告）日：2001-09-25

  Compounds of formula I are disclosed. as well as pharmaceutically acceptable salts thereof. The naphthosultam is substituted with various substituent groups including at least one cationic group -A-Q-L-B, wherein A-Q-L-B represents a side chain wherein: A is a C1-6 alkylene group, straight or branched, and optionally interrupted or terminated by 1-2 of —O—, —S—, NRa—, —C(O)— and —CH═CH—; Q represents  in which: b is 2 or 3; and X− is a charge balancing group; L represents a C1-8 alkylene group, unsubstituted or substituted with 1-3 Rc groups, and is interrupted or terminated by 1-3 of —CH═CH—, —C(O)—, —C(O)NRd—, —Het(Re)—, —C(O)—Het(Re)—, —C(O)NRa—Het(Re)—, —O—,—S—, —S(O)—, —SO2—, —CO2—, NRa—, —N+(Ra)2— B represents The carbapenems of the invention are effective against susceptible bacterial organisms, including methicillin resistant Staphylococcus aureus (MRSA), methicillin resistant Staphylococcus epidermidis (MRSE), and methicillin resistant coagulase negative Staphylococci (MRCNS).

  本文披露了化学式I的化合物及其药学上可接受的盐。其中，萘磺酰胺被各种取代基所取代，包括至少一个阳离子基团-A-Q-L-B，其中A-Q-L-B代表一个侧链，其中：A是一种C1-6烷基，直链或支链，并且可选地被1-2个-O-、-S-、NRa-、-C（O）-和-CH2CH-所中断或终止；Q代表-（CH2）b-，其中b为2或3；X-是一个平衡电荷的基团；L代表C1-8烷基，未取代或被1-3个Rc基团所取代，并且可被1-3个-CH2CH-、-C（O）-、-C（O）NRd-、-Het（Re）-、-C（O）-Het（Re）-、-C（O）NRa-Het（Re）-、-O-、-S-、-S（O）-、-SO2-、-CO2-、NRa-、-N+（Ra）2-所中断或终止；B代表本发明的碳青霉烯类抗生素对易感细菌有很好的效果，包括耐甲氧西林金黄色葡萄球菌（MRSA）、耐甲氧西林表皮葡萄球菌（MRSE）和耐甲氧西林凝血酶阴性葡萄球菌（MRCNS）。
• 1,8-naphthosultamylmethyl carbapenem antibacterial compounds, compositions containing such compounds and methods treatment
  申请人：Merck & Co., Inc.

  公开号：US06399597B1

  公开（公告）日：2002-06-04

  Compounds of formula I are disclosed. as well as pharmaceutically acceptable salts thereof. The naphthosultam is substituted with various substituent groups including at least one cationic group —A—Q—L—B. The carbapenems of the invention are effective against susceptible bacterial organisms, including methicillin resistant Staphylococcus aureus (MRSA), methicillin resistant Staphylococcus epidermidis (MRSE), and methicillin resistant coagulase negative Staphylococci (MRCNS).

  公开了式I的化合物以及其药学上可接受的盐。萘磺酰胺被各种取代基取代，包括至少一个阳离子基团-A-Q-L-B。发明中的头孢菌素对易感性细菌有作用，包括甲氧西林耐药的金黄色葡萄球菌（MRSA）、甲氧西林耐药的表皮葡萄球菌（MRSE）和甲氧西林耐药的凝血酶阴性葡萄球菌（MRCNS）。
• CP5484, a novel quaternary carbapenem with potent anti-MRSA activity and reduced toxicity
  作者：Takahisa Maruyama、Yasuo Yamamoto、Yuko Kano、Mizuyo Kurazono、Eiji Matsuhisa、Hiromi Takata、Toshihiko Takata、Kunio Atsumi、Katsuyoshi Iwamatsu、Eiki Shitara

  DOI：10.1016/j.bmc.2007.06.057

  日期：2007.10

  A new series of 1 beta-methyl carbapenems possessing a 6,7-disubstituted imidazo[5, 1-b]thiazol-2-yl group directly attached to the C-2 position of the carbapenem nucleus was prepared, and the activities of these compounds against methicillin-resistant Staphylococcus aureus (MRSA) were evaluated. To study the effect of basic moieties on anti-MRSA activity, we introduced an amino, or imino, or amidino group at the 6-position of imidazo[5,1-b]thiazole in place of the carbamoylmethyl moiety of CP5068. Anti-MRSA activities of almost all basic group-substituted carbapenems were improved, though some of the compounds showed stronger acute toxicity in mice than IPM. In order to decrease the toxicity without decreasing the activity, we introduced various additional functionalities around the basic moiety. Finally, we obtained CP5484, which has excellent anti-MRSA activity and low acute toxicity. (C) 2007 Elsevier Ltd. All rights reserved.