2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetyl chloride hydrochloride | 84208-30-0

• 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: 2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetyl chloride hydrochloride
• 英文别名: (4-nitrophenyl)methyl 2-[(Z)-[2-chloro-1-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxyacetate;hydrochloride
• CAS: 84208-30-0
• 化学式: C₁₆H₁₂Cl₂N₄O₇S*ClH
• 分子量: 511.727
• InChiKey: SDIWRJWBBNNZQQ-UXTSPRGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetyl chloride hydrochloride 在 palladium on activated charcoal sodium N-methyldithiocarbamate 、 三氧化硫 N,N-二甲基甲酰胺络合物 、 Dowex 500W 、 Dowex 50W 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 [1-(2-Amino-thiazol-4-yl)-1-((2S,3S)-2-methylcarbamoyl-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-meth-(Z)-ylideneaminooxy]-acetic acid
  参考文献：
  名称：

  Synthesis of carumonam (AMA-1080) and a related compound starting from (2R,3R)-epoxysuccinic acid.

  摘要：

  在对磺胺氟噻嗪进行化学改造的过程中，合成了几种4-氨甲酰-2-氮杂环丁酮-1-磺酸衍生物，旨在提高其抗菌活性。在这些化合物中，(3S, 4S)-3-[2-(2-氨噻唑-4-基)-(Z)-2-(1-羧基-1-甲基乙氧亚胺)乙酰氨基]-4-氨甲酰-2-氮杂环丁酮-1-磺酸(2)被发现对抗革兰氏阴性细菌具有强大的抗菌活性，结果与卡鲁莫南(1, AMA-1080; Ro 17-2301)相当。基于(2R, 3R)-环氧琥珀酸(5)这一易于获取的发酵产物，开发了高效的合成路径，以大规模制备1和2。

  DOI：

  10.1248/cpb.33.3798

文献信息

• 1-carboxymethoxy acetidinones and their production
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04794108A1

  公开（公告）日：1988-12-27

  A 2-azetidinone derivative having a group of the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each represents a hydrogen atom, alkyl, aryl or arylalkyl which may have a substituent at the 1-position and an amino group, at the 3-position, which may be acylated or protected, its salt or ester, and methods of producing the same, (1) a method comprising subjecting a 2-azetidinone derivative having a group of the formula ##STR2## wherein the symbols are as defined above at the 1-position and an amino group at the 3-position, its salt or ester to an acylation or protective-group introduction reaction, and (2) a method comprising reacting a 2-azetidinone derivative having a hydroxy group at the 1-position and an amino group, at the 3-position, which may be acylated or protected, or its salt with a compound of the formula ##STR3## wherein W is a halogen atom; other symbols are as defined above, its salt or ester. The above objective compounds are utilizable as excellent antimicrobial agents or as valuable intermediates for the synthesis of the same.

  一种2-吡咯酮衍生物，具有以下式子的基团：##STR1## 其中R.sup.1和R.sup.2相同或不同，分别代表氢原子，烷基，芳基或芳基烷基，可以在1-位取代基，并且在3-位具有氨基，可以酰化或保护，其盐或酯，以及制备其的方法，包括：(1)将具有以下式子的2-吡咯酮衍生物进行酰化或保护基引入反应：##STR2## 其中符号如上定义，在1-位有取代基，在3-位有氨基，其盐或酯；(2)将具有1-位羟基和在3-位具有氨基的2-吡咯酮衍生物或其盐与以下式子的化合物反应：##STR3## 其中W是卤素原子; 其他符号如上定义，其盐或酯。以上目标化合物可用作优异的抗微生物剂或用于合成相同的有价值的中间体。
• 1-Sulfo-2-oxoazetidine derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0053816A1

  公开（公告）日：1982-06-16

  A 1-sulfo-2-oxoazetidine derivative of formula wherein R is a residue derived from an organic compound by removal of one hydrogen atom attached to a carbon atom thereof; R' is an amino group which may optionally be , acylated or protected; X is hydrogen or methoxy, and methods of producing said compound (I) which may be written as follows or wherein the symbols have the same meanings as respectively defined above. The compound (I) has improved antimicrobial and β-lactamase-inhibitory activities and is of value as drugs for human beings and domesticated animals.

  一种 1-磺基-2-氧代氮杂环丁烷衍生物，其式中，R 是有机化合物的残基，通过去除连接到其碳原子上的一个氢原子而得到；R'是氨基，可任选被酰化或保护；X 是氢或甲氧基，以及生产所述化合物 (I) 的方法，其可如下写法或其中的符号分别具有与上述定义相同的含义。 该化合物 (I) 具有更好的抗菌活性和β-内酰胺酶抑制活性，具有作为人类和驯养动物药物的价值。
• 1-Sulfo-2-azetidinone derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0093376A2

  公开（公告）日：1983-11-09

  A 1-sulfo-2-oxoazetidine derivative of the formula wherein R8 is -COQ° (Q° is an amino group which may optionally be protected or substituted), -COQ5 (Q5 is a hydroxyl group which may optionally be protected), -(CH2)na- R4a (na is an integer of 1 to 3: R4a is a hydrogen atom or a carbamoylamino, N-sulfocarbamoylamino, carbamoyl, carbamoyloxy, N-sulfocarbamoyloxy, haloalkylcarbonylcarbamoyloxy, alkylsulfonyloxy, pyridinio, alkoxy, alkylsulfinyl, alkylsulfonyl, halogenoalkylcarbonyloxy, hydroxyl, alkoxycarbonyl, acyloxy, 1-alkoxyiminoalkyl, alkylcarbonyl or acylamino group) or a nitrogen-containing heterocyclic group; R' is an amino group which may optionally be acylated or protected; and X is a hydrogen atom or a methoxy group, or a salt or ester thereof, and methods of producing said compound (Ia) which may be shown as follows wherein the symbols have the same meanings as respectively defined above, and intermediates for preparing the compound (Ia) and methods of producing them. The compound (Ia) has improved antimicrobial and β-lactamase- inhibitory activities and is of value as drugs for human beings and domesticated animals.

  式中的 1-磺基-2-氧氮杂环丁烷衍生物 其中 R8 为-COQ°（Q°为氨基，可任选被保护或取代）、-COQ5（Q5 为羟基，可任选被保护）、-(CH2)na- R4a（na 为 1 至 3 的整数：R4a 是氢原子或氨基甲酰氨基、N-硫代氨基甲酰氨基、氨基甲酰基、氨基甲酰氧基、N-硫代氨基甲酰氧基、卤代烷基羰基氨基甲酰氧基、烷基磺酰氧基、吡啶基、烷氧基、烷基亚磺酰基、烷基磺酰基、卤代烷基羰基氧基、羟基、烷氧基羰基、酰氧基、1-烷氧基亚氨基烷基、烷基羰基或酰氨基）或含氮杂环基团；R'是可选择酰化或保护的氨基；X是氢原子或甲氧基，或其盐或酯，以及生产所述化合物（Ia）的方法，可如下所示 其中符号的含义分别与上述定义相同，以及制备化合物（Ia）的中间体及其生产方法。化合物（Ia）具有更好的抗菌和抑制β-内酰胺酶的活性，具有作为人类和驯养动物药物的价值。
• Azetidinones and their production
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0135194A1

  公开（公告）日：1985-03-27

  A 2-azetidinone derivative having a group of the formula wherein R' and R2 are the same or different and each represents a hydrogen atom, alkyl, aryl or arylalkyl which may have a substituent at the 1-position and an amino group, at the 3-position, which may be acylated or protected, its salts or ester, and methods of producing the same, (1) a method comprising subjecting a 2-azetidinone derivative having a group of the formula wherein the symbols are as defined above at the 1-position and an amino group at the 3-position, its salt or ester to an acylation or protective-group introduction reaction, and (2) a method comprising reacting a 2-azetidinone derivative having a hydroxy group at the 1-position and an amino group at the 3-position, which may be acylated or protected, or its salt with a compound of the formula wherein W is a halogen atom; other symbols are as defined above, its salt or ester. The above objective compounds are utilizable as excellent antimicrobial agents or as valuable intermediates for the synthesis of the same.

  一种 2-氮杂环丁酮衍生物，其基团的结构式为 其中R'和R2相同或不同，各自代表氢原子、烷基、芳基或芳基烷基，可在1位上有取代基，在3位上有氨基，可酰化或保护，其盐或酯，以及生产这种衍生物的方法、 (1)一种方法，包括将具有式中基团的 2-氮杂环丁酮衍生物 其中符号如上定义在 1 位，氨基在 3 位的 2-氮杂环丁酮衍生物、其盐或酯进行酰化或保护基引入反应，和 (2) 一种方法，包括使在 1 位上具有羟基和在 3 位上具有氨基的 2-氮杂环丁酮衍生物或其盐与式中化合物进行酰化或保护基团引入反应 其中 W 为卤素原子；其他符号如上定义；其盐或酯。上述目标化合物可用作优良的抗菌剂或合成抗菌剂的重要中间体。
• Tricyclic cepham compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0253337A2

  公开（公告）日：1988-01-20

  The compounds having a 4,11-dioxo-3-oxa8(or 7)-thia-1- azatricyclo[7,2,0,02,6]undecane-2-carboxylic acid skeleton as the base structure, their esters and their salts are useful antibacterial agents.

  以 4,11-二氧代-3-氧杂-8（或 7）-硫杂-1-氮杂三环[7,2,0,02,6]十一烷-2-羧酸骨架为基础结构的化合物、其酯类和盐类是有用的抗菌剂。