[carboxymethyl(4-methoxybenzenesulfonyl)amino]acetic acid | 59724-87-7

• 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: [carboxymethyl(4-methoxybenzenesulfonyl)amino]acetic acid
• 英文别名: 2-[carboxymethyl-(4-methoxyphenyl)sulfonylamino]acetic acid
• CAS: 59724-87-7
• 化学式: C₁₁H₁₃NO₇S
• mdl: MFCD02331437
• 分子量: 303.293
• InChiKey: PWOHLNQUNYXWPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [carboxymethyl(4-methoxybenzenesulfonyl)amino]acetic acid 在 N-甲基吗啉 、 氯甲酸乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 N-(4-methoxybenzenesulfonyl)-N-{[2-(4-sulfamoylphenyl)ethylcarbamoyl]methyl}-aminoacetohydroxamic acid
  参考文献：
  名称：

  碳酸酐酶抑制剂：亚氨基二乙酸羧酸盐/异羟肟酸酯也结合了苯磺酰胺部分，可抑制胞质/肿瘤相关的同工型I，II和IX。

  摘要：

  据报道，新型磺酰胺碳酸酐酶（CA，EC 4.2.1.1）抑制剂（CAI）的合成，其分子中还具有羧酸盐/异羟肟酸酯部分。这些化合物可能作用于双重抗肿瘤靶标，肿瘤相关的CA同工酶（CA IX）和某些基质金属蛋白酶（MMP）。这些化合物是从亚氨基二乙酸开始采用原始方法制备的，并作为三种同功酶hCA I，II（胞质）和IX（跨膜）的抑制剂进行了分析。新衍生物显示出对同工酶I（K（I）s在95-8300 nM范围内）的弱抑制活性，对中型CA II抑制剂（K（I）s在8.4-65 nM范围内）极好，并且非常好的选择性CA IX抑制剂（K（I）范围为3.8-26 nM）。

  DOI：

  10.1016/j.bmcl.2006.12.107
• 作为产物：
  描述：

  iminoacetic acid disodium salt monohydrate 、 对甲氧基苯磺酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 [carboxymethyl(4-methoxybenzenesulfonyl)amino]acetic acid
  参考文献：
  名称：

  Arylsulfonylamino hydroxamic acid derivatives

  摘要：

  式（I）的化合物，其中n、X、R.sup.3、R.sup.4和Ar如上所定义，可用于治疗所选疾病，包括关节炎、癌症、组织溃疡、再狭窄、牙周病、表皮溃疡性水疱病、巩膜炎和其他以基质金属蛋白酶活性为特征的疾病，艾滋病、败血症、脓毒性休克和其他涉及TNF产生的疾病。

  公开号：

  US05863949A1

文献信息

• Arylsulfonylamino hydroxamic acid derivatives
  申请人：Pfizer Inc

  公开号：US05863949A1

  公开（公告）日：1999-01-26

  A compound of formula (I), wherein n, X, R.sup.3, R.sup.4 and Ar are as defined above, useful in the treatment of a condition selected from the group consisting of arthritis, cancer, tissue ulceration, restenosis, periodontal disease, epidermolysis bullosa, scleritis and other diseases characterized by matrix metalloproteinase activity, AIDS, sepsis, septic shock and other diseases involving the production of TNF. ##STR1##

  式（I）的化合物，其中n、X、R.sup.3、R.sup.4和Ar如上所定义，可用于治疗所选疾病，包括关节炎、癌症、组织溃疡、再狭窄、牙周病、表皮溃疡性水疱病、巩膜炎和其他以基质金属蛋白酶活性为特征的疾病，艾滋病、败血症、脓毒性休克和其他涉及TNF产生的疾病。
• Method for controlling the growth of plants
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04070176A1

  公开（公告）日：1978-01-24

  A method for controlling the growth of plants, characterized by applying a plant growth regulator containing as active ingredient a benzenesulfonamide derivative represented by the general formula, ##STR1## wherein X is a halogen atom, an alkyl group having 1 to 5 carbon atoms, a nitro group, an amino group, an alkoxy group having 1 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, an alkylsulfonyl group having 1 to 5 carbon atoms, or a group of the formula R.sub.3 CONH-- (where R.sub.3 is an alkyl group having 1 to 5 carbon atoms); n is an integer of 0 to 5; R.sub.1 is hydrogen, an alkyl group having 1 to 5 carbon atoms, a phenyl group, a group of the formula --(A)--COOR.sub.4 [where R.sub.4 is hydrogen, an alkyl group having 1 to 5 carbon atoms, a cation such as Na.sup.+, K.sup.+, ammonium or a quaternary ammonium ion, and (A) is a group of the formula --(CH.sub.2).sub.m -- (where m is an integer of 1 to 3), or a group of the formula ##STR2## (where R.sub.5 and R.sub.6 are individually hydrogen or an alkyl group having 1 to 5 carbon atoms)]; and R.sub.2 is a straight chain, branched chain or alicyclic alkyl group having 1 to 15 carbon atoms, a hydroxyalkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a hydroxyl group, an aminoalkyl group having 1 to 5 carbon atoms, a cyano-C.sub.1-5 -alkyl, an alkenyl group having 2 to 5 carbon atoms, a C.sub.1-5 -alkoxy-C.sub.1-5 alkyl group, a sulfoalkyl group having 1 to 5 carbon atoms, a phenyl-substituted alkyl group having 1 to 5 carbon atoms, or a group of the formula --(A)--COOR.sub.4 (where R.sub.4 and (A) are as defined above), when R.sub.1 is hydrogen; is a hydroxyalkyl group having 1 to 5 carbon atoms, a group of the formula --(A)--COOR.sub.4 (where R.sub.4 and (A) are as defined above), a group of the formula --(B)--OOCR.sub.7 [where R.sub.7 is a phenyl group or an alkyl group having 1 to 5 carbon atoms, and (B) is a group of the formula (CH.sub.2).sub.j -- (where j is an integer of 1 to 3), or a group of the formula ##STR3## (where R.sub.5 and R.sub.6 are as defined above)], when R.sub.1 is an alkyl group having 1 to 5 carbon atoms; and is a group of the formula --(A)--COOR.sub.4 (where R.sub.4 and (A) are as defined above), when R.sub.1 is a phenyl group or a group of the formula --(A)--COOR.sub.4 (where R.sub.4 and (A) are as defined above).

  一种控制植物生长的方法，其特征在于施用一种植物生长调节剂，其活性成分为一种苯磺酰胺衍生物，其通式表示为##STR1##其中，X是卤素原子、具有1至5个碳原子的烷基、硝基、氨基、具有1至5个碳原子的烷氧基、具有1至5个碳原子的烷硫基、具有1至5个碳原子的烷基磺酰基或式R.sub.3 CONH--（其中R.sub.3是具有1至5个碳原子的烷基）的基团；n是0至5的整数；R.sub.1是氢、具有1至5个碳原子的烷基、苯基、式--(A)--COOR.sub.4[其中R.sub.4是氢、具有1至5个碳原子的烷基、如Na.sup. +，K.sup. +，铵或季铵离子等阳离子，(A)是式--(CH.sub.2).sub.m--（其中m是1至3的整数），或式##STR2##（其中R.sub.5和R.sub.6分别是氢或具有1至5个碳原子的烷基）]的基团；R.sub.2是具有1至15个碳原子的直链、支链或脂环烷基、具有1至5个碳原子的羟基烷基、具有1至5个碳原子的卤代烷基、羟基、具有1至5个碳原子的氨基烷基、氰基-C.sub.1-5-烷基、具有2至5个碳原子的烯基、C.sub.1-5-烷氧基-C.sub.1-5-烷基、具有1至5个碳原子的磺酰基烷基、具有1至5个碳原子的苯基取代烷基或式--(A)--COOR.sub.4（其中R.sub.4和（A）如上所定义），当R.sub.1是氢时；是具有1至5个碳原子的羟基烷基、式--(A)--COOR.sub.4（其中R.sub.4和（A）如上所定义）、式--(B)--OOCR.sub.7[其中R.sub.7是苯基或具有1至5个碳原子的烷基，(B)是式(CH.sub.2).sub.j--（其中j是1至3的整数），或式##STR3##（其中R.sub.5和R.sub.6如上所定义），当R.sub.1是具有1至5个碳原子的烷基时；是式--(A)--COOR.sub.4（其中R.sub.4和（A）如上所定义），当R.sub.1是苯基或式--(A)--COOR.sub.4（其中R.sub.4和（A）如上所定义）时。
• Dual Inhibitors of Matrix Metalloproteinases and Carbonic Anhydrases: Iminodiacetyl-Based Hydroxamate−Benzenesulfonamide Conjugates
  作者：Sérgio M. Marques、Elisa Nuti、Armando Rossello、Claudiu T. Supuran、Tiziano Tuccinardi、Adriano Martinelli、M. Amélia Santos

  DOI：10.1021/jm800964f

  日期：2008.12.25

  Matrix metalloproteinases (MMPs) and carbonic anhydrases (CAs) are two classes of zinc enzymes with different roles and catalytic targets, such as the degradation of most of the extracellular matrix (ECM) proteins and the regulation of the CO2/HCO3- equilibrium in the cells, respectively. Both families have isoforms which were proved to be involved in several stages of carcinogenic processes, and so the selective inhibition of these enzymes might be of interest in cancer therapy. We report herein the design, synthesis, and in vitro evaluation of a series Of Compounds possessing the iminodiacetic acid as the main backbone and two functional groups attached, namely, the hydroxamic acid and the arylsulfonamide (ArSO2NH2) moieties, to enable the inhibition of MMPs and CAs, respectively. These compounds were demonstrated to strongly inhibit both MMPs and CAs, some of them from the nanomolar to subnanomolar range. Furthermore, a docking study for MMPs was reported for the most promising compound in order to investigate its binding interactions with the different MMPs.
• TRBD-Binding Effectors and Methods for Using the Same to Modulate Telomerase Activity
  申请人：Skordalakes Emmanuel

  公开号：US20100160260A1

  公开（公告）日：2010-06-24

  The present invention embraces compounds selected for interacting with the T-pocket of telomerase and use thereof for modulating the activity of telomerase and preventing or treating diseases or conditions associated with telomerase.
• Screening Method and Compounds for Modulating Telomerase Activity
  申请人：Skordalakes Emmanuel

  公开号：US20120309759A1

  公开（公告）日：2012-12-06

  The present invention embraces methods for identifying compounds that modulate the activity of telomerase. Compounds of the invention are identified by designing or screening for a compound which binds to at least one amino acid residue of the TRBD, “thumb,” “finger,” and/or “palm” domain; or FP-pocket, PT-pocket or Th-pocket of telomerase and testing the compound for its ability to modulate the activity of telomerase. Compounds selected for interacting with the T-pocket or Fingers-Palm pocket of telomerase are also provided.